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Syn/anti lateral protonation
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- Author: ^^^Wim Nerinckx^^^
- Responsible Curator: ^^^Spencer Williams^^^
Overview
This page will provide a table (and eventually a full lexicon article) on the spatial positioning of the catalytic general acid residue in the active sites of glycoside hydrolases. The table below updates those found in the seminal paper on this concept by Heightman and Vasella [1], and the more recent summary by Nerinckx et al. [2].
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 page tab above the page title.
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)8 | beta | retaining | anti | 4pbg | 6-phospho-beta-galactosidase | Lactococcus lactis | product | Glu160 | Glu375 | [3] |
GH2 | A | (β/α)8 | beta | retaining | anti | 1jz0 | beta-galactosidase | Escherechia coli | 2-F-galactosyl | Glu461 | Glu537 | [4] |
GH3 | none | (β/α)8 | beta | retaining | anti | 1iew | exo-1,3-1,4-glucanase | Hordeum vulgare | 2-F-glucosyl | Glu491 | Asp285 | [5] |
GH5 | A | (β/α)8 | beta | retaining | anti | 1iew | endo-1,4-glucanase | Bacillus agaradhaerans | 2-F-glucosyl | Glu129 | Glu228 | [6] |
GH6 | none | (β/α)8 | beta | inverting | syn | 1ocn | cellobiohydrolase | Humicola insolens | Glc-isofagomine | Asp226 | debated | [7] |
GH7 | B | β-jelly roll | beta | retaining | syn | 1ovw | endo-1,4-glucanase | Fusarium oxysporum | Michaelis thio-Glc5 | Glu202 | Glu197 | [8] |
GH8 | M | (α/α)6 | beta | inverting | anti | 1kwf | endo-1,4-glucanase | Clostridium thermocellum | Michaelis | Glu95 | Asp278 | [9] |
GH9 | none | (α/α)6 | beta | inverting | syn | 3tf4, 4tf4 | cellulase | Thermomonospora fusca | product | Glu424 | Asp55, Asp58 | [10] |
GH10 | A | (β/α)8 | beta | retaining | anti | 2xyl | xylanase B (Cex) | Cellulomonas fimi | Xyl-2-F-xylosyl | Glu127 | Glu233 | [11] |
GH11 | C | β-jelly roll | beta | retaining | syn | 1bvv | xylanase | Bacillus circulans | Xyl-2-F-xylosyl | Glu172 | Glu78 | [12] |
GH12 | C | β-jelly roll | beta | retaining | syn | 2nlr | endo-1,4-glucanase | Streptomyces lividans | Glc2-2-F-glucosyl | Glu203 | Glu120 | [13] |
GH13 | H | (β/α)8 | alpha | retaining | anti | 1ckx | beta-cyclodextrin glucanotransferase | Bacillus circulans | Michaelis | Glu257 | Asp229 | [14] |
GH14 | none | (β/α)8 | alpha | inverting | syn | 1b9z | beta-amylase | Bacillus cereus | product | Glu172 | Glu367 | [15] |
GH15 | L | (α/α)6 | alpha | inverting | syn | 1gah | glucoamylase | Aspergillus awamori | acarbose | Glu179 | Glu400 | [16] |
GH16 | B | β-jelly roll | beta | retaining | syn | 1urx | beta-agarase A | Zobellia galactanivorans | product | Glu152 | Glu147 | [17] |
GH17 | A | (β/α)8 | beta | retaining | anti by similarity | |||||||
GH18 | K | (β/α)8 | beta | retaining | anti | 1ffr | chitinase A | Serratia marcescens | Michaelis (NAG)6 | Glu315 | internal | [18] |
GH20 | K | (β/α)8 | beta | retaining | anti | 1c7s | chitobiase | Serratia marcescens | Michaelis chitobiose | Glu540 | internal | [19] |
GH22 | none | lysozyme type | beta | retaining | syn | 1h6m | lysozyme C | Gallus gallus | Chit-2-F-chitosyl | Glu35 | Asp52 | [20] |
GH23 | none | lysozyme type | beta | inverting | syn | 1lsp | lysozyme G | Cygnus atratus | Bulgecin A | Glu73 | internal | [21] |
GH24 | I | α + β | beta | inverting | syn | 148l | lysozyme E | Bacteriophage T4 | chitobiosyl | Glu11 | Glu26 | [22] |
GH26 | A | (β/α)8 | beta | retaining | anti | 1gw1 | mannanase A | Cellvibrio japonicus | (Man2)-2-F-mannosyl | Glu212 | Glu320 | [23] |
GH27 | D | (β/α)8 | alpha | retaining | anti | 1ktc | α-N-acetyl galactosaminidase | Gallus gallus | NAGal | Asp201 | Asp410 | [24] |
GH29 | none | (β/α)8 | alpha | retaining | syn | 1hl9 | α-L-fucosidase | Thermotoga maritima | 2-F-fucopyranosyl | Glu266 | Asp224 | [25] |
GH30 | A | (β/α)8 | beta | retaining | anti by similarity | |||||||
GH31 | D | (β/α)8 | alpha | retaining | anti | 1xsk | α-xylosidase | Escherechia coli | 5-F-xylosyl | Asp482 | Asp416 | [26] |
GH32 | J | 5-fold β-propeller | alpha | retaining | anti | 2add | fructan β-(2,1)-fructosidase | Cichorium intybus | sucrose | Glu201 | Asp22 | [27] |
GH33 | E | 6-fold β-propeller | alpha | retaining | anti | 1s0k | trans-sialidase | Trypanosoma cruzi | 2-F,3-F-sialosyl | Asp59 | Tyr342 | [28] |
GH34 | E | 6-fold β-propeller | alpha | retaining | anti | 2bat | neuraminidase | Influenza A virus | sialic acid | Asp151 | Tyr406 | [29] |
GH35 | A | (β/α)8 | beta | retaining | anti by similarity | |||||||
GH37 | G | (α/α)6 | alpha | inverting | anti | 2jf4 | trehalase | Escherechia coli | validoxylamine | Asp312 | Glu496 | [30] |
GH38 | none | (β/α)7 | alpha | retaining | anti | 1qwn | α-mannosidase II | Drosophila melanogaster | 5-F-β-L-gulosyl | Asp341 | Asp204 | [31] |
GH39 | A | (β/α)8 | beta | retaining | anti | 1uhv | β-xylosidase | Thermoanaerobacterium saccharolyticum | 2-F-xylosyl | Glu160 | Glu277 | [32] |
GH42 | A | (β/α)8 | beta | retaining | anti | 1kwk | β-galactosidase | Thermus thermophylus A4 | galactose | Glu141 | Glu312 | [33] |
GH44 | none | (β/α)8 | beta | retaining | anti | 2eqd | endoglucanase | Clostridium thermocellum | cellooctaose | Glu186 | Glu359 | [34] |
GH45 | none | six-stranded β-barrel | beta | inverting | syn | 4eng | endo-1,4-glucanase | Humicola insolens | product | Asp121 | Asp10 | [35] |
GH46 | I | α + β | beta | inverting | syn by similarity | |||||||
GH47 | none | (α/α)7 | alpha | inverting | anti | 1x9d | α-mannosidase I | Homo sapiens | Michaelis | Asp463 | Glu599 | [36], [37] |
GH48 | M | (α/α)6 | beta | inverting | anti by similarity | |||||||
GH50 | A | (β/α)8 | beta | retaining | anti by similarity | |||||||
GH51 | A | (β/α)8 | alpha | retaining | anti | 1pz2 | α-L-arabinofuranosidase | Geobacillus stearothermophilus | L-arabinofuranosyl | Glu175 | Glu294 | [38] |
GH53 | A | (β/α)8 | beta | retaining | anti by similarity | |||||||
GH54 | none | β-sandwich | alpha | retaining | anti | 1wd4 | α-L-arabinofuranosidase B | Aspergillus kawachii | L-arabinofuranose | Asp297 | Glu221 | [39] |
GH56 | none | (β/α)7 | beta | retaining | anti | 1fcv | hyaluronidase | Apis mellifera | (hyaluron.)4 | Glu113 | internal | [40] |
GH57 | none | (β/α)7 | alpha | retaining | anti | 1kly | glucanotransferase | Thermococcus litoralis | acarbose | Asp214 | Glu123 | [41] |
GH59 | A | (β/α)8 | beta | retaining | anti by similarity | |||||||
GH63 | G | (α/α)6 | alpha | inverting | anti by similarity | |||||||
GH65 | L | (α/α)6 | alpha | inverting | syn by similarity | |||||||
GH67 | none | (β/α)8 | alpha | inverting | syn | 1gql | α-glucuronidase | Cellvibrio japonicus Ueda107 | glucuronic acid | Glu292 | unknown | [42] |
GH68 | J | 5-fold β-propeller | beta | retaining | anti | 1pt2 | levansucrase | Bacillus subtilis | sucrose | Glu342 | Asp86 | [43] |
GH70 | H | (β/α)8 | alpha | retaining | anti by similarity | |||||||
GH72 | A | (β/α)8 | beta | retaining | anti by similarity | |||||||
GH74 | none | 7-fold β-propeller | beta | inverting | syn | 2ebs | cellobiohydrolase (OXG-RCBH) | Geotrichum sp. m128 | xyloglucan heptasaccharide | Asp465 | Asp35 | [44] |
GH77 | H | (β/α)8 | alpha | retaining | anti | 1esw | amylomaltase | Thermus aquaticus | acarbose | Asp395 | Asp293 | [45] |
GH79 | A | (β/α)8 | beta | retaining | anti by similarity | |||||||
GH80 | I | α + β | beta | inverting | syn by similarity | |||||||
GH83 | E | 6-fold β-propeller | alpha | retaining | anti by similarity | |||||||
GH85 | K | (β/α)8 | beta | retaining | anti by similarity | |||||||
GH86 | A | (β/α)8 | beta | retaining | anti by similarity | |||||||
GH89 | none | (β/α)8 | alpha | retaining | anti | 2vcb | α-N-acetylglucosaminidase | Clostridium perfringens | PUGNAc | Glu483 | Glu601 | [46] |
GH92 | none | (α/α)6 + beta-sandwich | alpha | inverting | anti | 2ww1 | α-1,2-mannosidase | Bacteroides thetaiotaomicron VPI-5482 | thiomannobioside | Glu533 | Asp462 | [47] |
GH93 | E | 6-fold β-propeller | alpha | retaining | anti by similarity | |||||||
GH94 | none | (α/α)6 | beta | inverting | syn | 1v7x | chitobiose phosphorylase | Vibrio proteolyticus | GlcNAc | Asp492 | phosphate | [48] |
GH95 | none | (α/α)6 | alpha | inverting | anti | 2ead | α-1,2-L-fucosidase | Bifibacterium bifidum | substrate | Glu566 | Asn423 Asp766 | [49] |
GH102 | none | double-psi beta-barrel | beta | retaining | syn | 2pi8 | lytic transglycosylase A | Escherechia coli | chitohexaose | Asp308 | none | [50] |
GH113 | A | (β/α)8 | beta | retaining | anti by similarity |
References
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Zhu et al. (2010) Nature Chemical Biology in the press; DOI: 10.1038/nchembio.278 direct link.
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