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Literature summary for 4.1.2.17 extracted from

  • Garrabou, X.; Gomez, L.; Joglar, J.; Gil, S.; Parella, T.; Bujons, J.; Clapes, P.
    Structure-guided minimalist redesign of the L-fuculose-1-phosphate aldolase active site: expedient synthesis of novel polyhydroxylated pyrrolizidines and their inhibitory properties against glycosidases and intestinal disaccharidases (2010), Chemistry, 16, 10691-10706.
    View publication on PubMed
Search for more literature for 4.1.2.17

Cloned(Commentary)

Cloned (Comment) Organism
expressed in Escherichia coli M-15 [pREP-4] cells Escherichia coli

Protein Variants

Protein Variants Comment Organism
F131A the mutant has 1% retroaldol activity with L-fuculose-1-phosphate as compared to the wild type enzyme. The mutant uses (R)-N-benzyloxycarbonyl-prolinal as substrate and is highly stereoselective both with (R)-and with (S)-N-benzyloxycarbonyl-prolinal, exclusively producing the anti- and syn-aldol adducts, respectively Escherichia coli
F131A/Del(207-215) inactive Escherichia coli
F131A/F206A the relative activity of F131A/F206A towards L-fuculose-1-phosphate is approximately less than 0.5% as compared to the wild type enzyme Escherichia coli
F131A/Y113A inactive Escherichia coli
F206A the mutant has 22% retroaldol activity with L-fuculose-1-phosphate as compared to the wild type enzyme Escherichia coli
additional information the deletion mutants Del(211-215) and Del(207-215) show 11% and 2% retroaldol activity with L-fuculose-1-phosphate, respectively, as compared to the wild type enzyme Escherichia coli
Y113A the mutant has 0.5% retroaldol activity with L-fuculose-1-phosphate as compared to the wild type enzyme Escherichia coli

Inhibitors

Inhibitors Comment Organism Structure
1,4-dideoxy-1,4-imino-L-arabinitol
-
 Escherichia coli
1,4-dideoxy-1,4-iminod-arabinitol
-
 Escherichia coli
D-fagomine
-
 Escherichia coli
L-fagomine
-
 Escherichia coli

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-

Purification (Commentary)

Purification (Comment) Organism
ammonium sulfate precipitation Escherichia coli

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
dihydroxyacetone + (R)-N-benzyloxycarbonyl-alaninal
-
 Escherichia coli 5-[[(benzyloxy)carbonyl]amino]-5,6-dideoxy-1-O-phosphonato-D-erythro-hex-2-ulose
-
 ?
dihydroxyacetone + (S)-N-benzyloxycarbonyl-alaninal
-
 Escherichia coli 5-[[(benzyloxy)carbonyl]amino]-5,6-dideoxy-1-O-phosphonato-D-erythro-hex-2-ulose
-
 ?
dihydroxyacetone + benzyl (2R)-2-formylpyrrolidine-1-carboxylate
-
 Escherichia coli (3R,4R)-4-[1-[(benzyloxy)carbonyl]pyrrolidin-2-yl]-3,4-dihydroxy-2-oxobutyl phosphate
-
 ?
dihydroxyacetone + benzyl (2S)-2-formylpyrrolidine-1-carboxylate
-
 Escherichia coli (3R,4S)-4-[1-[(benzyloxy)carbonyl]pyrrolidin-2-yl]-3,4-dihydroxy-2-oxobutyl phosphate
-
 ?
dihydroxyacetone + benzyl [(2R)-3-methyl-1-oxobutan-2-yl]carbamate
-
 Escherichia coli (3R,4R,5R)-5-[[(benzyloxy)carbonyl]amino]-3,4-dihydroxy-6-methyl-2-oxoheptyl phosphate
-
 ?
dihydroxyacetone + benzyl [(2R)-4-methyl-1-oxopentan-2-yl]carbamate
-
 Escherichia coli (3R,4R,5R)-5-[[(benzyloxy)carbonyl]amino]-3,4-dihydroxy-7-methyl-2-oxooctyl phosphate
-
 ?
dihydroxyacetone + benzyl [(2S)-3-methyl-1-oxobutan-2-yl]carbamate
-
 Escherichia coli (3R,4R,5R)-5-[[(benzyloxy)carbonyl]amino]-3,4-dihydroxy-6-methyl-2-oxoheptyl phosphate + (3R,4S,5R)-5-[[(benzyloxy)carbonyl]amino]-3,4-dihydroxy-6-methyl-2-oxoheptyl phosphate 70:30 product ratio ?
dihydroxyacetone + benzyl [(2S)-4-methyl-1-oxopentan-2-yl]carbamate
-
 Escherichia coli (3R,4R,5R)-5-[[(benzyloxy)carbonyl]amino]-3,4-dihydroxy-7-methyl-2-oxooctyl phosphate
-
 ?
dihydroxyacetone + benzyl [(3S)-3-methyl-1-oxopentan-2-yl]carbamate
-
 Escherichia coli (3R,4R,5R,6S)-5-(((benzyloxy)carbonyl)amino)-3,4-dihydroxy-6-methyl-2-oxooctyl phosphate + (3R,4S,5R,6S)-5-(((benzyloxy)carbonyl)amino)-3,4-dihydroxy-6-methyl-2-oxooctyl phosphate 78:22 product ratio ?
L-fuculose 1-phosphate
-
 Escherichia coli dihydroxyacetone phosphate + (S)-lactaldehyde
-
 ?
additional information (R)-N-benzyloxycarbonyl-prolinal is not a substrate for the wild type enzyme Escherichia coli ?
-
 ?

Synonyms

Synonyms Comment Organism
FucA
-
 Escherichia coli
L-fuculose-1-phosphate aldolase
-
 Escherichia coli