View source for Syn/anti lateral protonation

{{CuratorApproved}}
* [[Author]]: [[User:Wim Nerinckx|Wim Nerinckx]]
* [[Responsible Curator]]:  [[User:Spencer Williams|Spencer Williams]]

----

== Overview ==

This page provides a table that summarizes the spatial positioning of the catalytic [[general acid]] residue in the active sites of [[glycoside hydrolase]]s, relative to the substrate. The table below updates those found in the seminal paper on this concept by Heightman and Vasella <cite>HeightmanVasella1999</cite>, and a following paper by Nerinckx ''et al.'' <cite>Nerinckx2005</cite>.

== Background ==

The ''"not from above, but from the side"'' concept of semi-lateral glycosidic oxygen [[General_acid/base|protonation]] by [[glycoside hydrolase]]s was introduced by Heightman and Vasella <cite>HeightmanVasella1999</cite>. It was originally only described for [[Anomeric centre (alpha and beta)|beta]]-equatorial [[glycoside hydrolase]]s, but appears to be equally applicable to enzymes acting on an [[Anomeric centre (alpha and beta)|alpha]]-axial glycosidic bond <cite>Nerinckx2005</cite>. When dividing [[Sub-site nomenclature|subsite -1]] into half-spaces by a plane defined by the glycosidic oxygen and C1' and H1' of the –1 glycoside, many ligand-complexed structures reveal that the [[General_acid/base|proton donor]] is positioned either in the ''syn'' half-space (near the ring-oxygen of the –1 glycoside), or in the ''anti'' half-space (on the opposite side of the ring-oxygen). Members of the same GH [[Families|family]] appear to share a common ''syn'' or ''anti'' [[General_acid/base|protonator]] arrangement and further, this specificity appears to be preserved within [[Clans|Clans]] of [[Families|families]]. This page's compilation of [[Sub-site nomenclature|subsite -1]] occupied complexes shows that about 70% of all GH [[Families|families]] are ''anti'' [[General_acid/base|protonators]].

Closer inspection of crystal structures of [[Sub-site nomenclature|–1/+1 subsite]]-spanning substrates, or substrate-analogue ligands, in complex with enzymes reveals a further intriguing corollary <cite>Nerinckx2005 Wu2012</cite>. In substrate-bound complexes with ''anti'' [[General_acid/base|protonating]] GH enzymes, the scissile [[Anomeric centre (alpha and beta)|anomeric bond]] (often studied using the thio-analogue) shows a dihedral angle φ (O5'-C1'-[O,S]x-Cx) that is in the lowest-energy synclinal (gauche) conformation. The rationale for this is that a minus synclinal dihedral angle φ for an equatorial glycosidic bond, or plus synclinal for an axial glycosidic bond <cite>Perez1978</cite>, allows for hyperconjugative overlap of the C1'-O5' antibonding orbital with an antiperiplanar-oriented lone pair orbital lobe of the glycosidic oxygen, thereby creating partial double bond character and stabilization of the glycosidic bond by 4–5 kcal/mol; this ground-state stabilizing phenomenon is known as the ‘exo-anomeric effect’ <cite>Cramer1997 Johnson2009 Alonso2016</cite>. ''Anti'' [[General_acid/base|protonation]] occurs on the glycosidic oxygen’s antiperiplanar lone pair, thereby removing the stabilizing exo-anomeric effect. This suggests that ''anti'' [[General_acid/base|protonation]] is an enzymic approach for lowering the activation barrier leading to the [[Transition state|transition state]] (Figure 1 centre).

''Syn'' [[General_acid/base|protonating]] [[glycoside hydrolase]]s apparently make use of a different approach <cite>Nerinckx2005 Wu2012</cite>. In many [[Sub-site nomenclature|–1/+1 subsite]]-spanning ligand complexes, the dihedral angle φ of the scissile anomeric bond has been rotated away from its lowest-energy synclinal position: clockwise to minus-anticlinal or antiperiplanar for beta-equatorial; counterclockwise to plus-anticlinal or antiperiplanar for alpha-axial [[Anomeric centre (alpha and beta)|anomeric bonds]]. This removes the hyperconjugative overlap and thus also the stabilizing exo-anomeric effect. And because of this rotation, a lone pair of the glycosidic oxygen is directed into the ''syn'' half-space, allowing it to be protonated by the ''syn''-positioned [[General_acid/base|proton donor]] (Figure 1 right).

[[File:Syn_anti.jpg|800px|thumb|center|Figure 1. Newman projections, with the glycosidic oxygen as proximal atom and the anomeric carbon as distal atom, showing ''anti'' (centre) versus ''syn'' (right) semi-lateral [[General_acid/base|protonation]] in beta-equatorial (top) and alpha-axial (bottom) [[glycoside hydrolase]]s. The indicated φ is the dihedral angle for O5'-C1'-O4-C4.]]

== Table of ''syn/anti'' protonation examples ==

This table contains only one example per GH [[Families|family]] of a ligand-complexed protein structure where the ''syn'' or ''anti'' positioning of the [[General_acid/base|proton donor]] can be clearly observed; other examples may be available on a [[Families|family-by-family]] basis. The reader is thus advised to consult the [http://www.cazy.org/fam/acc_GH.html#table CAZy database] for a current, comprehensive list of CAZyme structures. Where available, the selected examples are Michaelis-type complexes with the ligand spanning the [[Sub-site nomenclature|-1/+1 subsites]], since these have an intact glycosidic or thioglycosidic bond, or are ''N''-analogs of the substrate (''e.g.'' acarbose). In some examples, the [[General_acid/base|proton donor]] has been mutated (''e.g.'', to the corresponding amide or to an alanine), and in those cases one may wish to look at a superposition of the given PDB example with the structure of the native enzyme. If a Michaelis-type complex is not yet available, the second and third example choices, respectively, are trapped glycosyl-enzyme [[intermediate]]s and product complexes where [[Sub-site nomenclature|subsite -1]] is occupied.

''Please also be aware that this is a large table with many data. Please contact the page Author or Responsible Curator with corrections.''

=== Table ===
This table can be re-sorted by clicking on the icons in the header (''javascript must be turned on in your browser'').  To reset the page to be sorted by GH family, click the ''View'' tab at the very top of the page.

{| {{Prettytable}} class="sortable"
|- valign="top"
! '''Family'''
! '''Clan'''
! '''Structure fold   '''
! '''Anomeric specificity'''
! '''Mechanism'''
! '''''Syn/anti'' protonator'''
! '''Example PDB ID'''
! '''Enzyme'''
! '''Organism'''
! '''Ligand'''
! '''General acid'''
! '''Nucleophile or General base'''
! '''Reference'''
|-
| [[GH1]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}2cer 2cer]
| β-glycosidase S
| ''Sulfolobus solfataricus'' P2
| phenethyl glucoimidazole
| '''Glu206'''
| Glu387
| <cite>Gloster2006</cite>
|-
| [[GH2]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}} / alpha-{{Smallcaps|l}}
| retaining
| '''''anti'''''
| [{{PDBlink}}2vzu 2vzu]
| exo-β-glucosaminidase
| ''Amicolatopsis orientalis''
| PNP-β-{{Smallcaps|d}}-glucosamine
| '''Glu469'''
| Glu541
| <cite>van_Bueren2009</cite>
|-
| [[GH3]]
| none
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}} / alpha-{{Smallcaps|l}}
| retaining
| '''''anti'''''
| [{{PDBlink}}1iex 1iex]
| exo-1,3-1,4-glucanase
| ''Hordeum vulgare''
| thiocellobiose
| '''Glu491'''
| Asp285
| <cite>Hrmova2001</cite>
|-
| [[GH4]]
| none
| Rossmann + α6/β3 + β3/α4
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}1u8x 1u8x]
| 6-P-α-glucosidase
| ''Bacillus subtilis''
| alpha-{{Smallcaps|d}}-glucose-6-phosphate
| '''Asp172'''
| not applicable
| <cite>Rajan2004</cite>
|-
| [[GH5]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}1h2j 1h2j]
| endo-β-1,4-glucanase
| ''Bacillus agaradhaerens''
| 2',4'-DNP-2-F-cellobioside
| '''Glu129'''
| Glu228
| <cite>Varrot2003</cite>
|-
| [[GH6]]
| none
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| inverting
| '''''syn'''''
| [{{PDBlink}}1qjw 1qjw]
| cellobiohydrolase 2
| ''Hypocrea jecorina''
| (Glc)<sub>2</sub>-S-(Glc)<sub>2</sub>
| '''Asp221'''
| debated
| <cite>Zhou1999</cite>
|-
| [[GH7]]
| B
| β-jelly roll
| beta-{{Smallcaps|d}}
| retaining
| '''''syn'''''
| [{{PDBlink}}1ovw 1ovw]
| endo-1,4-glucanase
| ''Fusarium oxysporum''
| thio-(Glc)<sub>5</sub>
| '''Glu202'''
| Glu197
| <cite>Sulzenbacher1999</cite>
|-
| [[GH8]]
| M
| (α/α)<sub>6</sub>
| beta-{{Smallcaps|d}}
| inverting
| '''''anti'''''
| [{{PDBlink}}1kwf 1kwf]
| endo-1,4-glucanase
| ''Clostridium thermocellum''
| cellopentaose
| '''Glu95'''
| Asp278
| <cite>Guerin2002</cite>
|-
| [[GH9]]
| none
| (α/α)<sub>6</sub>
| beta-{{Smallcaps|d}}
| inverting
| '''''syn'''''
| [{{PDBlink}}1rq5 1rq5]
| cellobiohydrolase
| ''Clostridium thermocellum''
| cellotetraose
| '''Glu795'''
| Asp383
| <cite>Schubot2004</cite>
|-
| [[GH10]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}2d24 2d24]
| β-1,4-xylanase
| ''Streptomyces olivaceoviridis'' E-86
| xylopentaose
| '''Glu128'''
| Glu236
| <cite>Suzuki2009</cite>
|-
| [[GH11]]
| C
| β-jelly roll
| beta-{{Smallcaps|d}}
| retaining
| '''''syn'''''
| [{{PDBlink}}4hk8 4hk8]
| endo-β-1,4-xylanase
| ''Hypocrea jecorina''
| xylohexaose
| '''Glu177'''
| Glu86
| <cite>Wan2014</cite>
|-
| [[GH12]]
| C
| β-jelly roll
| beta-{{Smallcaps|d}}
| retaining
| '''''syn'''''
| [{{PDBlink}}1w2u 1w2u]
| endoglucanase
| ''Humicola grisea''
| thiocellotetraose
| '''Glu205'''
| Glu120
| <cite>Sandgren2004</cite>
|-
| [[GH13]]
| H
| (β/α)<sub>8</sub>
| alpha-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}1cxk 1cxk]
| β-cyclodextrin glucanotransferase
| ''Bacillus circulans''
| maltononaose
| '''Glu257'''
| Asp229
| <cite>Uitdehaag1999</cite>
|-
| [[GH14]]
| none
| (β/α)<sub>8</sub>
| alpha-{{Smallcaps|d}}
| inverting
| '''''syn'''''
| [{{PDBlink}}1itc 1itc]
| β-amylase
| ''Bacillus cereus''
| maltopentaose
| '''Glu172'''
| Glu367
| <cite>Miyake2003</cite>
|-
| [[GH15]]
| L
| (α/α)<sub>6</sub>
| alpha-{{Smallcaps|d}}
| inverting
| '''''anti'''''
| [{{PDBlink}}1dog 1dog]
| glucoamylase
| ''Aspergillus awamori''
| 1-deoxynojirimycin
| '''Glu179'''
| Glu400
| <cite>Harris1993</cite>
|-
| [[GH16]]
| B
| β-jelly roll
| beta-{{Smallcaps|d}}
| retaining
| '''''syn'''''
| [{{PDBlink}}1urx 1urx]
| β-agarase A
| ''Zobellia galactanivorans''
| oligoagarose
| '''Glu152'''
| Glu147
| <cite>Allouch2004</cite>
|-
| [[GH17]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}4gzj 4gzj]
| endo-β-1,3-glucanase
| ''Solanum tuberosum''
| laminaratriose + laminarabiose
| '''Glu118'''
| Glu259
| <cite>Wojtkowiak2013</cite>
|-
| [[GH18]]
| K
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}1ffr 1ffr]
| chitinase A
| ''Serratia marcescens''
| (NAG)<sub>6</sub>
| '''Glu315'''
| internal
| <cite>Papanikolau2001</cite>
|-
| [[GH19]]
| none
| lysozyme type
| beta-{{Smallcaps|d}}
| inverting
| '''''syn'''''
| [{{PDBlink}}3wh1 3wh1]
| chitinase
| ''Bryum coronatum''
| (GlcNAc)<sub>4</sub>
| '''Glu61'''
| Glu70
| <cite>Ohnuma2014</cite>
|-
| [[GH20]]
| K
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}1c7s 1c7s]
| chitobiase
| ''Serratia marcescens''
| chitobiose
| '''Glu540'''
| internal
| <cite>Prag2000</cite>
|-
| [[GH22]]
| none
| lysozyme type
| beta-{{Smallcaps|d}}
| retaining
| '''''syn'''''
| [{{PDBlink}}1h6m 1h6m]
| lysozyme C
| ''Gallus gallus''
| Chit-2-F-chitosyl
| '''Glu35'''
| Asp52
| <cite>Vocadlo2001</cite>
|-
| [[GH23]]
| none
| lysozyme type
| beta-{{Smallcaps|d}}
| inverting
| '''''syn'''''
| [{{PDBlink}}1lsp 1lsp]
| lysozyme G
| ''Cygnus atratus''
| Bulgecin A
| '''Glu73'''
| internal
| <cite>Karlsen1996</cite>
|-
| [[GH24]]
| I
| α + β
| beta-{{Smallcaps|d}}
| inverting
| '''''syn'''''
| [{{PDBlink}}148l 148l]
| lysozyme E
| Bacteriophage T4
| chitobiosyl
| '''Glu11'''
| Glu26
| <cite>Baldwin1993</cite>
|-
| [[GH26]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}2vx6 2vx6]
| exo-β-mannanase
| ''Cellvibrio japonicus'' Ueda107
| Gal1Man4
| '''Glu221'''
| Glu338
| <cite>Cartmell2008</cite>
|-
| [[GH27]]
| D
| (β/α)<sub>8</sub>
| alpha-{{Smallcaps|d}} / beta-{{Smallcaps|l}}
| retaining
| '''''anti'''''
| [{{PDBlink}}3lrm 3lrm]
| α-galactosidase
| ''Saccharomyces cerevisiae''
| raffinose
| '''Asp209'''
| Asp141
| <cite>Fernandez-Leiro2010</cite>
|-
| [[GH28]]
| N
| β-helix
| alpha-{{Smallcaps|d}} (and α-{{Smallcaps|l}}-rham)
| inverting
| '''''anti'''''
| [{{PDBlink}}2uvf 2uvf]
| exo-polygalacturonosidase
| ''Yersinia enterocolitica'' ATCC9610D
| digalacturonic acid
| '''Asp402'''
| Asp381 Asp403
| <cite>Abbott2007</cite>
|-
| [[GH29]]
| R
| (β/α)<sub>8</sub>
| alpha-{{Smallcaps|l}}
| retaining
| '''''syn'''''
| [{{PDBlink}}3uet 3uet]
| α-1,3/4-fucosidase
| ''Bifidobacterium longum'' subsp. infantis
| lacto-''N''-fucopentaose II
| '''Glu217'''
| Asp172
| <cite>Sakurama2012</cite>
|-
| [[GH30]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}2y24 2y24]
| glucurono-xylanase
| ''Dickea chrysanthemi'' D1
| glucuronoxylan tetrasaccharide
| '''Glu163'''
| Glu253
| <cite>Urbanikova2011</cite>
|-
| [[GH31]]
| D
| (β/α)<sub>8</sub>
| alpha-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}2qmj 2qmj]
| maltase-glucoamylase
| ''Homo sapiens''
| acarbose
| '''Asp542'''
| Asp443
| <cite>Sim2008</cite>
|-
| [[GH32]]
| J
| 5-fold β-propeller
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}2add 2add]
| fructan β-(2,1)-fructosidase 
| ''Cichorium intybus''
| sucrose
| '''Glu201'''
| Asp22
| <cite>Verhaest2007</cite>
|-
| [[GH33]]
| E
| 6-fold β-propeller
| alpha-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}1s0i 1s0i]
| transsialidase
| ''Trypanosoma cruzi''
| sialyllactose
| '''Asp59'''
| Tyr342
| <cite>Amaya2004</cite>
|-
| [[GH34]]
| E
| 6-fold β-propeller
| alpha-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}4gzw 4gzw]
| N2 neuraminidase
| ''Influenza'' A Tanzania/205/2010 H3N2
| α-{{Smallcaps|d}}-Neup5Ac-(2,3)-β-{{Smallcaps|d}}-Galp-(1,4)-β-{{Smallcaps|d}}-GlcpNAc
| '''Asp151'''
| Tyr406
| <cite>Zhu2012</cite>
|-
| [[GH35]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}3ogv 3ogv]
| β-galactosidase
| ''Hypocrea jecorina''
| 2-phenylethyl 1-thio-β-{{Smallcaps|d}}-galactopyranoside
| '''Glu200'''
| Glu298
| <cite>Maksimainen2011</cite>
|-
| [[GH36]]
| D
| (β/α)<sub>8</sub>
| alpha-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}4fnu 4fnu]
| β-galactosidase
| ''Geobacillus stearothermophilus''
| stachyose
| '''Asp584'''
| Asp478
| <cite>Merceron2012</cite>
|-
| [[GH37]]
| G
| (α/α)<sub>6</sub>
| alpha-{{Smallcaps|d}}
| inverting
| '''''anti'''''
| [{{PDBlink}}2jf4 2jf4]
| trehalase
| ''Escherichia coli''
| validoxylamine
| '''Asp312'''
| Glu496
| <cite>Gibson2007</cite>
|-
| [[GH38]]
| none
| (β/α)<sub>7</sub>
| alpha-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}3czn 3czn]
| Golgi α-mannosidase II
| ''Drosophila melanogaster''
| GlcNAcMan(5)GlcNAc(2)
| '''Asp341'''
| Asp204
| <cite>Shah2008</cite>
|-
| [[GH39]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}} / alpha-{{Smallcaps|l}}
| retaining
| '''''anti'''''
| [{{PDBlink}}2bfg 2bfg]
| β-xylosidase
| ''Geobacillus stearothermophilus''
| 2,5-dinitrophenyl-β-{{Smallcaps|d}}-xyloside
| '''Glu160'''
| Glu278
| <cite>Czjzek2005</cite>
|-
| [[GH42]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}} / alpha-{{Smallcaps|l}}
| retaining
| '''''anti'''''
| [{{PDBlink}}4ucf 4ucf]
| β-galactosidase
| ''Bifidobacterium bifidum''
| {{Smallcaps|d}}-galactose
| '''Glu161'''
| Glu320
| <cite>Godoy2016</cite>
|-
| [[GH43]]
| F
| 5-fold β-propeller
| beta-{{Smallcaps|d}} / alpha-{{Smallcaps|l}}
| inverting
| '''''anti'''''
| [{{PDBlink}}3akh 3akh]
| exo-1,5-α-{{Smallcaps|l}}-arabinofuranosidase
| ''Streptomyces avermitilis''
| α-1,5-arabinofuranotriose
| '''Glu196'''
| Asp220
| <cite>Fujimoto2010</cite>
|-
| [[GH44]]
| none
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}2eqd 2eqd]
| endoglucanase
| ''Clostridium thermocellum''
| cellooctaose
| '''Glu186'''
| Glu359
| <cite>Kitago2007</cite>
|-
| [[GH45]]
| none
| 6-stranded β-barrel
| beta-{{Smallcaps|d}}
| inverting
| '''''syn'''''
| [{{PDBlink}}4eng 4eng]
| endo-1,4-glucanase
| ''Humicola insolens''
| cellohexaose
| '''Asp121'''
| Asp10
| <cite>Davies1996</cite>
|-
| [[GH46]]
| I
| lysozyme type
| beta-{{Smallcaps|d}}
| inverting
| '''''syn'''''
| [{{PDBlink}}4olt 4olt]
| chitosanase
| ''Microbacterium sp.'' OU01
| hexa-glucosamine
| '''Glu25'''
| Asp43
| <cite>Lyu2014</cite>
|-
| [[GH47]]
| none
| (α/α)<sub>7</sub>
| alpha-{{Smallcaps|d}}
| inverting
| '''''anti'''''
| [{{PDBlink}}1x9d 1x9d]
| α-mannosidase I
| ''Homo sapiens''
| Me-2-S-(α-Man)-2-thio-α-Man
| '''Asp463'''
| Glu599
| <cite>Karaveg2005</cite>, <cite>Nerinckx2008</cite>
|-
| [[GH48]]
| M
| (α/α)<sub>6</sub>
| beta-{{Smallcaps|d}}
| inverting
| ''predicted anti by clan''
| ''see at GH8''
| 
| 
| 
| 
| 
| 
|-
| [[GH49]]
| N
| β-helix
| alpha-{{Smallcaps|d}}
| inverting
| ''predicted anti by clan''
| ''see at GH28''
| 
| 
| 
| 
| 
| 
|-
| [[GH50]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}4bq5 4bq5] 
| exo-β-agarase
| ''Saccharophagus degradans''
| neoagarotetraose
| '''Glu535'''
| Glu695
| <cite>Pluvinage2013</cite>
|-
| [[GH51]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}} / alpha-{{Smallcaps|l}}
| retaining
| '''''anti'''''
| [{{PDBlink}}1qw9 1qw9]
| α-{{Smallcaps|l}}-arabinofuranosidase
| ''Geobacillus stearothermophilus''
| PNP-{{Smallcaps|l}}-arabinofuranoside
| '''Glu175'''
| Glu294
| <cite>Hoevel2003</cite>
|-
| [[GH52]]
| O
| (α/α)<sub>6</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}4c1p 4c1p]
| β-xylosidase
| ''Geobacillus thermoglucosidasius''
| xylobiose
| '''Asp517'''
| Glu537
| <cite>Espina2014</cite>
|-
| [[GH53]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}2ccr 2ccr]
| β-1,4-galactanase
| ''Bacillus licheniformis''
| galactotriose
| '''Glu165'''
| Glu263
| <cite>Le_Nours2009</cite>
|-
| [[GH54]]
| none
| β-sandwich
| beta-{{Smallcaps|d}} / alpha-{{Smallcaps|l}}
| retaining
| '''''anti'''''
| [{{PDBlink}}1wd4 1wd4]
| α-{{Smallcaps|l}}-arabinofuranosidase B
| ''Aspergillus kawachii''
| {{Smallcaps|l}}-arabinofuranose
| '''Asp297'''
| Glu221
| <cite>Miyanaga2004</cite>
|-
| [[GH55]]
| none
| β-helix
| beta-{{Smallcaps|d}}
| inverting
| '''''syn'''''
| [{{PDBlink}}4tz5 4tz5]
| exo-β-1,3-glucanase
| ''Streptomyces sp.'' SirexAA-E
| laminarihexaose
| '''Glu502'''
| unknown
| <cite>Bianchetti2015</cite>
|-
| [[GH56]]
| none
| (β/α)<sub>7</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}1fcv 1fcv]
| hyaluronidase
| ''Apis mellifera''
| (hyaluron.)<sub>4</sub>
| '''Glu113'''
| internal
| <cite>Markovic-Housley2000</cite>
|-
| [[GH57]]
| none
| (β/α)<sub>7</sub>
| alpha-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}1k1y 1k1y]
| glucanotransferase
| ''Thermococcus litoralis''
| acarbose
| '''Asp214'''
| Glu123
| <cite>Imamura2003</cite>
|-
| [[GH59]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}4ccc 4ccc]
| β-galactocerebrosidase
| ''Mus musculus''
| PNP-β-{{Smallcaps|d}}-galactoside
| '''Glu182'''
| Glu258
| <cite>Hill2013</cite>
|-
| [[GH62]]
| F
| 5-fold β-propeller
| alpha-{{Smallcaps|l}}
| inverting
| '''''anti'''''
| [{{PDBlink}}3wn0 3wn0]
| α-{{Smallcaps|l}}-arabinofuranosidase
| ''Streptomyces coelicolor''
| β-{{Smallcaps|l}}-Arabinofuranose
| '''Glu361'''
| Asp202
| <cite>Maehara2014</cite>
|-
| [[GH63]]
| G
| (α/α)<sub>6</sub>
| alpha-{{Smallcaps|d}}
| inverting
| '''''anti'''''
| [{{PDBlink}}5ca3 5ca3]
| α-glucosidase
| ''Escherichia coli''
| glucose and lactose
| '''Asp501'''
| Glu727
| <cite>Miyazaki2016</cite>
|-
| [[GH65]]
| L
| (α/α)<sub>6</sub>
| alpha-{{Smallcaps|d}} (and α-{{Smallcaps|l}}-rham)
| inverting
| '''''anti'''''
| [{{PDBlink}}4ktr 4ktr]
| 2-O-α-glucosylglycerol phosphorylase
| ''Bacillus selenitireducens''
| isofagomine
| '''Glu475'''
| phosphate
| <cite>Touhara2014</cite>
|-
| [[GH66]]
| none
| (β/α)<sub>8</sub>
| alpha-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}5axh 5axh]
| dextranase
| ''Thermoanaerobacter pseudethanolicus''
| isomaltohexaose
| '''Glu374'''
| Asp312
| <cite>Suzuki2016</cite>
|-
| [[GH67]]
| none
| (β/α)<sub>8</sub>
| alpha-{{Smallcaps|d}}
| inverting
| '''''syn'''''
| [{{PDBlink}}1l8n 1l8n]
| α-glucuronidase
| ''Geobacillus stearothermophilus''
| 4-O-methyl-{{Smallcaps|d}}-glucuronic acid and xylotriose
| '''Glu286'''
| Asp364 Glu392
| <cite>Golan2004</cite>
|-
| [[GH68]]
| J
| 5-fold β-propeller
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}1pt2 1pt2]
| levansucrase
| ''Bacillus subtilis''
| sucrose
| '''Glu342'''
| Asp86
| <cite>Meng2003</cite>
|-
| [[GH70]]
| H
| (β/α)<sub>8</sub>
| alpha-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}3aic 3aic]
| glucansucrase
| ''Streptococcus mutans''
| α-acarbose
| '''Glu515'''
| Asp477
| <cite>Ito2011</cite>
|-
| [[GH72]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}2w62 2w62]
| β-1,3-glucanotransferase
| ''Saccharomyces cerevisiae'' S288C
| laminaripentaose
| '''Glu176'''
| Glu275
| <cite>Hurtado-Gerrero2009</cite>
|-
| [[GH74]]
| none
| 7-fold β-propeller
| beta-{{Smallcaps|d}}
| inverting
| '''''syn'''''
| [{{PDBlink}}2ebs 2ebs]
| cellobiohydrolase (OXG-RCBH)
| ''Geotrichum sp.'' m128
| xyloglucan heptasaccharide
| '''Asp465'''
| Asp35
| <cite>Yaoi2007</cite>
|-
| [[GH76]]
| none
| (α/α)<sub>6</sub>
| alpha-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}5agd 5agd]
| endo-α-1,6-mannanase
| ''Bacillus circulans''
| α-1,6-mannopentaose
| '''Asp125'''
| Asp124
| <cite>Thompson2015</cite>
|-
| [[GH77]]
| H
| (β/α)<sub>8</sub>
| alpha-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}2oww 2oww]
| 4-α-glucanotransferase
| ''Thermus thermofilus''
| acarbose + 4-deoxy-α-{{Smallcaps|d}}-glucose
| '''Glu340'''
| Asp293
| <cite>Barends2007</cite>
|-
| [[GH78]]
| H
| (α/α)<sub>6</sub>
| alpha-{{Smallcaps|l}}
| inverting
| '''''anti'''''
| [{{PDBlink}}3w5n 3w5n]
| α-{{Smallcaps|l}}-rhamnosidase
| ''Streptomyces avermitilis''
| {{Smallcaps|l}}-rhamnose
| '''Glu636'''
| Glu895
| <cite>Fujimoto2013</cite>
|-
| [[GH79]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}5e9c 5e9c]
|  heparanase
| ''Homo sapiens''
| heparin tetrasaccharide
| '''Glu225'''
| Glu343
| <cite>Wu2015</cite>
|-
| [[GH80]]
| I
| α + β
| beta-{{Smallcaps|d}}
| inverting
| ''predicted syn by clan''
| ''see at GH24''
| 
| 
| 
| 
| 
|
|-
| [[GH81]]
| none
| β-sandwich
| beta-{{Smallcaps|d}}
| inverting
| '''''syn'''''
| [{{PDBlink}}5t4g 5t4g]
| endo-β-1,3-glucanase
| ''Bacillus halodurans'' C-125
| laminarin
| '''Asp466'''
| Glu542
| <cite>Pluvinage2017</cite>
|-
| [[GH83]]
| E
| 6-fold β-propeller
| alpha-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}1z4x 1z4x]
| hemagglutinin-neuraminidase
| Simian virus 5
| α-2,3-sialyllactose
| '''Glu247''' relay
| Tyr523
| <cite>Yuan2005</cite>
|-
| [[GH84]]
| none
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}2chn 2chn]
| β-''N''-acetyl-glucosaminidase
| ''Bacteroides thetaiotaomicron'' VPI-5482
| NAG-thiazoline
| '''Glu242'''
| internal
| <cite>Dennis2006</cite>
|-
| [[GH85]]
| K
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}2w92 2w92]
| endo-β-''N''-acetyl-glucosaminidase D
| ''Streptococcus pneumoniae'' TIGR4
| NAG-thiazoline
| '''Glu337'''
| internal
| <cite>Abbott2009</cite>
|-
| [[GH86]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}4aw7 4aw7]
| β-porphyranase
| ''Bacteroides plebeius''
| porphyran fragment
| '''Glu152'''
| Glu279
| <cite>Hehemann_1_2012</cite>
|-
| [[GH89]]
| none
| (β/α)<sub>8</sub>
| alpha-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}2vcb 2vcb]
| α-''N''-acetyl-glucosaminidase
| ''Clostridium perfringens''
| PUGNAc
| '''Glu483'''
| Glu601
| <cite>Ficko-Blean2008</cite>
|-
| [[GH92]]
| none
| (α/α)<sub>6</sub> and β-sandwich
| alpha-{{Smallcaps|d}}
| inverting
| '''''anti'''''
| [{{PDBlink}}2ww1 2ww1]
| α-1,2-mannosidase
| ''Bacteroides thetaiotaomicron'' VPI-5482
| thiomannobioside
| '''Glu533'''
| Asp644 Asp642
| <cite>Zhu2009</cite>
|-
| [[GH93]]
| E
| 6-fold β-propeller
| alpha-{{Smallcaps|l}}
| retaining
| '''''anti'''''
| [{{PDBlink}}3a72 3a72]
| exo-arabinanase
| ''Penicillium chrysogenum''
| arabinobiose
| '''Glu246'''
| Glu174
| <cite>Sogabe2011</cite>
|-
| [[GH94]]
| Q
| (α/α)<sub>6</sub>
| beta-{{Smallcaps|d}}
| inverting
| '''''syn'''''
| [{{PDBlink}}4zli 4zli]
| cellobionic acid phosphorylase
| ''Saccharophagus degradans''
| 3-O-β-{{Smallcaps|d}}-glucopyranosyl-α-{{Smallcaps|d}}-glucopyranuronic acid
| '''Asp472'''
| phosphate
| <cite>Nam2015</cite>
|-
| [[GH95]]
| none
| (α/α)<sub>6</sub>
| alpha-{{Smallcaps|l}}
| inverting
| '''''anti'''''
| [{{PDBlink}}2ead 2ead]
| α-1,2-{{Smallcaps|l}}-fucosidase
| ''Bifidobacterium bifidum''
| Fuc-α-1,2-Gal
| '''Glu566'''
| Asn423 Asp766
| <cite>Nagae2007</cite>
|-
| [[GH97]]
| none
| (β/α)<sub>8</sub>
| alpha-{{Smallcaps|d}}
| retaining + inverting
| '''''anti'''''
| [{{PDBlink}}2zq0 2zq0]
| α-glucosidase
| ''Bacteroides thetaiotaomicron'' VPI-5482
| acarbose
| '''Glu532'''
| Glu508
| <cite>Kitamura2008</cite>
|-
| [[GH98]]
| none
| (β/α)<sub>8</sub> and β-sandwich
| beta-{{Smallcaps|d}}
| inverting
| '''''anti'''''
| [{{PDBlink}}2wmg 2wmg]
| endo-β-1,4-galactosidase
| ''Streptococcus pneumoniae''
| A-Lewis<sup>Y</sup> pentasaccharide
| '''Glu158'''
| Asp251 Glu301
| <cite>Higgins2009</cite>
|-
| [[GH99]]
| none
| (β/α)<sub>8</sub>
| alpha-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}4ad4 4ad4]
| endo-α-mannosidase
| ''Bacteroides xylanisolvens''
| glucose-1,3-isofagomine and α-1,2- mannobiose
| '''Glu336'''
| debated
| <cite>Thompson2012</cite>
|-
| [[GH100]] 
| none
| (α/α)<sub>6</sub> core
| beta-{{Smallcaps|d}}
| inverting
| '''''anti'''''
| [{{PDBlink}}5gop 5gop]
| invertase
| ''Anabaena (Nostoc) sp.'' pcc7120 
| sucrose
| '''Asp188'''
| Glu414
| <cite>Xie2016</cite>
|-
| [[GH102]]
| none
| double-ψ β-barrel
| beta-{{Smallcaps|d}}
| retaining
| '''''syn'''''
| [{{PDBlink}}2pi8 2pi8]
| lytic transglycosylase A
| ''Escherichia coli''
| chitohexaose
| '''Asp308'''
| none
| <cite>van_Straaten2007</cite>
|-
| [[GH103]]
| none
| lysozyme type
| beta-{{Smallcaps|d}}
| retaining
| '''''syn'''''
| [{{PDBlink}}1d0k 1d0k]
| lytic transglycosylase SLT35
| ''Escherichia coli''
| murodipeptides
| '''Glu162'''
| internal
| <cite>van_Asselt2000</cite>
|-
| [[GH106]]
| none
| (β/α)<sub>8</sub>
| alpha-{{Smallcaps|l}}
| inverting
| '''''anti'''''
| [{{PDBlink}}5mwk 5mwk]
| α-{{Smallcaps|l}}-rhamnosidase BT_0986
| ''Bacteroides thetaiotaomicron''
| pectin heptasaccharide
| '''Glu461'''
| Glu593 or Glu561
| <cite>Ndeh2017</cite>
|-
| [[GH107]]
| R
| (β/α)<sub>8</sub>
| alpha-{{Smallcaps|l}}
| retaining
| ''predicted syn by clan''
| ''see at GH29''
| 
| 
| 
| 
| 
|
|-
| [[GH110]]
| none
| parallel β-helix
| alpha-{{Smallcaps|d}}
| inverting
| '''''anti'''''
| [{{PDBlink}}7jwf 7jwf]
| α-1,3-galactosidase
| ''Pseudoalteromonas distincta''
| Gal-α1,3-Gal
| '''Asp344'''
| Asp321 Asp345
| <cite>McGuire2020</cite>
|-
| [[GH113]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}4cd8 4cd8]
| β-mannanase
| ''Alicyclobacillus acidocaldarius''
| mannobioimidazole
| '''Glu151'''
| Glu231
| <cite>Williams2014</cite>
|-
| [[GH116]]
| O
| (α/α)<sub>6</sub> and β-sandwich
| beta-{{Smallcaps|d}}
| retaining
| ''predicted anti by clan''
| ''see at GH52''
| 
| 
| 
| 
| 
| 
|-
| [[GH117]]
| none
| 5-fold β-propeller
| alpha-{{Smallcaps|l}}
| inverting
| '''''anti'''''
| [{{PDBlink}}4ak7 4ak7]
| α-1,3-3,6-anhydro-{{Smallcaps|l}}-galactosidase
| ''Bacteroides plebeius''
| neoagarobiose
| '''His302''' (relay from Asp320)
| Asp90
| <cite>Hehemann_2_2012</cite>
|-
| [[GH120]]
| none
| parallel β-helix and β-sandwich
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}3vsv 3vsv]
| β-xylosidase XylC
| ''Thermoanaerobacterium saccharolyticum'' JW/SL-YS485
| {{Smallcaps|d}}-xylose
| '''Glu405'''
| Asp382
| <cite>Huang2012</cite>
|-
| [[GH123]]
| none
| (β/α)<sub>8</sub> and β-sandwich
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}5fr0 5fr0]
| exo-β-N-acetyl-galactosaminidase
| ''Clostridium perfringens''
| ''N''-difluoroacetyl-{{Smallcaps|d}}-galactosamine
| '''Glu345'''
| internal
| <cite>Noach2016</cite>
|-
| [[GH125]]
| L
| (α/α)<sub>6</sub>
| alpha-{{Smallcaps|d}}
| inverting
| '''''anti'''''
| [{{PDBlink}}5m7y 5m7y]
| exo-α-1,6-mannosidase
| ''Clostridium perfringens''
| 1,6-α-mannotriose
| '''Asp220'''
| Glu393
| <cite>Alonso-Gil2016</cite>
|-
| [[GH127]]
| P
| (α/α)<sub>6</sub> and β-sandwich
| beta-{{Smallcaps|l}}
| retaining
| '''''anti'''''
| [{{PDBlink}}3wrg 3wrg]
| β-{{Smallcaps|l}}-arabinofuranosidase
| ''Bifidobacterium longum''
| {{Smallcaps|l}}-arabinose
| '''Glu322'''
| Cys417
| <cite>Huang2014</cite>
|-
| [[GH128]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}6ufl 6ufl]
| β-1,3-glucanase
| ''Amycolatopsis mediterranei''
| laminarihexaose
| '''Glu102'''
| Glu199
| <cite>Santos2020</cite>
|-
| [[GH130]]
| none
| 5-fold β-propeller
| beta-{{Smallcaps|d}}
| inverting
| '''''anti'''''
| [{{PDBlink}}5b0s 5b0s]
| β-1,2-mannobiose phosphorylase
| ''Listeria innocua''
| β-1,2-mannotriose
| '''Asp141''' relay
| phosphate
| <cite>Tsuda2015</cite>
|-
|  [[GH134]]
| none
| β + α
| beta-{{Smallcaps|d}}
| inverting
| '''''syn'''''
| [{{PDBlink}}5jug 5jug]
| β-mannanase
| ''Streptomyces sp.''
| mannopentaose
| '''Glu45'''
| Asp57
| <cite>Jin2016</cite>
|-
|  [[GH136]]
| none
| β-helix
| beta-{{Smallcaps|d}}
| retaining
| '''''syn'''''
| [{{PDBlink}}5gqf 5gqf]
| lacto-N-biosidase
| ''Bifidobacterium longum''
| lacto-N-biose
| '''Asp411'''
| Asp418
| <cite>Yamada2017</cite>
|-
|  [[GH137]]
| none
| 5-fold β-propeller
| beta-{{Smallcaps|l}}
| unknown
| '''''anti'''''
| [{{PDBlink}}5mui 5mui]
| β-{{Smallcaps|l}}-arabinofuranosidase BT_0996
| ''Bacteroides thetaiotaomicron''
| pectin oligosaccharide
| '''Glu240'''
| Glu159
| <cite>Ndeh2017</cite>
|-
|  [[GH138]]
| none
| (β/α)<sub>8</sub>
| alpha-{{Smallcaps|d}}
| retaining
| '''''syn'''''
| [{{PDBlink}}6hzg 6hzg]
| α-1,2-{{Smallcaps|d}}-galacturonidase
| ''Bacteroides paurosaccharolyticus''
| alpha-{{Smallcaps|d}}-galactopyranuronic
| '''Glu294'''
| Glu361
| <cite>Labourel2019</cite>
|-
| [[GH146]]
| P
| (α/α)<sub>6</sub> and β-sandwich
| beta-{{Smallcaps|l}}
| retaining
| '''''anti'''''
| [{{PDBlink}}5opj 5opj]
| β-{{Smallcaps|l}}-arabinofuranosidase BT_0349
| ''Bacteroides thetaiotaomicron''
| {{Smallcaps|l}}-arabinose
| '''Glu320'''
| Cys416
| <cite>Luis2018</cite>
|-
| [[GH147]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| ''predicted anti by clan''
| ''see at e.g. GH1''
| 
| 
| 
| 
| 
|
|-
| [[GH148]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| ''predicted anti by clan''
| ''see at e.g. GH1''
| 
| 
| 
| 
| 
|
|-
| [[GH149]]
| Q
| (α/α)<sub>6</sub>
| beta-{{Smallcaps|d}}
| inverting
| ''predicted syn by clan''
| ''see at GH94''
| 
| 
| 
| 
| 
| 
|-
| [[GH156]]
| none
| (β/α)<sub>8</sub>
| alpha-{{Smallcaps|d}}
| inverting
| '''''syn'''''
| [{{PDBlink}}6s0e 6s0e]
| exo-α-sialidase
| uncultured bacterium pG7
| N-acetyl-2,3-dehydro-2-deoxyneuraminic acid
| '''His134''' (relay from Asp132)
| Asp14
| <cite>Bule2019</cite>
|-
| [[GH157]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| ''predicted anti by clan''
| ''see at e.g. GH1''
| 
| 
| 
| 
| 
| 
|-
| [[GH158]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| ''predicted anti by clan''
| ''see at e.g. GH1''
| 
| 
| 
| 
| 
| 
|-
| [[GH161]]
| Q
| (α/α)<sub>6</sub>
| beta-{{Smallcaps|d}}
| retaining
| ''predicted syn by clan''
| ''see at GH94''
| 
| 
| 
| 
| 
| 
|-
| [[GH162]]
| none
| (α/α)<sub>6</sub>
| beta-{{Smallcaps|d}}
| inverting
| '''''syn'''''
| [{{PDBlink}}6imw 6imw]
| endo-β-1,2-glucanase
| ''Talaromyces funiculosus''
| beta-1,2-glucan
| '''Glu262''' via C3-OH of glc at subs. +2
| Asp446
| <cite>Tanaka2019</cite>
|-
| [[GH164]]
| A
| (β/α)<sub>8</sub>
| beta-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}6t75 6t75]
| β-mannosidase
| ''Bacteroides salyersiae''
| 2-deoxy-2-F-mannosyl
| '''Glu160''' 
| Glu297
| <cite>Armstrong2020</cite>
|-
| [[GH172]]
| none
| β-jelly roll
| alpha-{{Smallcaps|d}}
| retaining
| '''''anti'''''
| [{{PDBlink}}7v1w 7v1w]
| difructose-anhydride synthase
| ''Bifidobacterium dentum''
| beta-{{Smallcaps|d}}-arabinofuranose
| '''Glu270''' 
| Glu291
| <cite>Kashima2021</cite>
|-
| [http://www.cazy.org/GH0.html n.c.*]
| none
| parallel β-helix
| alpha-{{Smallcaps|d}}
| inverting
| '''''anti'''''
| [{{PDBlink}}2vjj 2vjj]
| endo-α-N-acetylglucosaminidase
| Bacteriophage HK620
| O18A1 O-antigen hexasaccharide
| '''Asp339'''
| Glu372
| <cite>Barbirz2008</cite>
|}
<nowiki>*</nowiki> n.c.: Found among the collection of [http://www.cazy.org/GH0.html non-classified GH sequences in the CAZy Database].

== References ==

<biblio>
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# Nerinckx2005 pmid=15642336
# Wu2012 pmid=23137336
# Perez1978 Pérez S and Marchessault RH. ''The exo-anomeric effect: experimental evidence from crystal structures.'' Carbohydr res. 1978 65:114-120. [http://dx.doi.org/10.1016/S0008-6215(00)84218-4 DOI:10.1016/S0008-6215(00)84218-4]
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</biblio>

[[Category:Definitions and explanations]]