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Literature summary for 3.2.1.146 extracted from

  • Oliveira Udry, G.A.; Repetto, E.; Vega, D.R.; Varela, O.
    Synthesis of enantiomeric polyhydroxyalkylpyrrolidines from 1,3-dipolar cycloadducts. Evaluation as inhibitors of a beta-galactofuranosidase (2016), J. Org. Chem., 81, 4179-4189 .
    View publication on PubMed
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Inhibitors

Inhibitors Comment Organism Structure
additional information synthesis of enantiomeric polyhydroxyalkylpyrrolidines from 1,3-dipolar cycloadducts by the 1,3-dipolar cycloaddition of sugar enones with azomethine ylides derived from natural amino acids, and evaluation as inhibitors of a beta-galactofuranosidase, overview. Reduction of the ketone carbonyl group of the cycloadducts, which possess a basic structure of bicyclic 6-(menthyloxy)hexahydropyrano[4,3-c]pyrrol-7(6H)one, affords a number of pyrrolidine-based bicyclic systems. The unprotected products are isolated as pyrrolidinium trifluoroacetates. Because of the furanose-like nature of the target trihydroxyalkyl pyrrolidines, these molecules are evaluated as inhibitors of the beta-galactofuranosidase from Penicillium fellutanum. The compounds ((2R,3S,3aR,6aS)-1-[(tert-butyloxy)carbonyl]-3-(1'(S),2'-diacetoxyethyl)-6-acetoxy-2-phenylhexahydro-1H-furo[3,4-b]pyrrole, (2S,3R,3aS,6aR)-1-[(tert-butyloxy)carbonyl]-3-(1'(R),2'-diacetoxyethyl)-6-acetoxy-2-phenylhexahydro-1H-furo[3,4-b]pyrrole, (2S,3R,4S,5R)-4-(1'(S),2'-diacetoxyethyl)-2,3-bis(acetoxymethyl)-1-[(tert-butyloxy)carbonyl]-5-phenylpyrrolidine, (2R,3S,4R,5S)-4-(1'(R),2'-diacetoxyethyl)-2,3-bis(acetoxymethyl)- 1-[(tert-butyloxy)carbonyl]-5-phenylpyrrolidine, (2S,3R,4S,5R)-4-(1'(S),2'-dihydroxyethyl)-2,3-bis(hydroxymethyl)-5-phenylpyrrolidinium trifluoroacetate, (2R,3S,4R,5S)-4-(1'(R),2'-dihydroxyethyl)-2,3-bis(hydroxymethyl)-5-phenylpyrrolidinium trifluoroacetate, (1R,3aR,4S,6R,6aS)-5-[(tert-butyloxy)carbonyl]-4-(hydroxymethyl)-6-phenylhexahydro-1H-furo[3,4-c]pyrrol-1-ol, (1S,3aS,4R,6S,6aR)-5-[(tert-butyloxy)carbonyl]-4-(hydroxymethyl)-6-phenylhexahydro-1H-furo[3,4-c]pyrrol-1-ol, (2S,3R,4S,5R)-1-[(tert-butyloxy)carbonyl]-2,3,4-tris-(hydroxymethyl)-5-phenylpyrrolidine, (2R,3S,4R,5S)-1-[(tert-butyloxy)carbony l]-2,3,4-tris-(hydroxymethyl)-5-phenylpyrrolidine, (2S,3R,4S,5R)-2,3,4-tris(hydroxymethyl)-5-phenylpyrrolidinium trifluoroacetate, and (2R,3S,4R,5S)-2,3,4-tris(hydroxymethyl)-5-phenylpyrrolidinium trifluoroacetate) show practically no inhibitory activity for concentration of pyrrolidines in the range of 0.1-1.6 mM. NMR structure analysis Penicillium fellutanum

Organism

Organism UniProt Comment Textmining
Penicillium fellutanum
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-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-nitrophenyl beta-D-galactofuranoside + H2O
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 Penicillium fellutanum 4-nitrophenol + D-galactofuranose
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 ?

Synonyms

Synonyms Comment Organism
beta-D-galactofuranosidase
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 Penicillium fellutanum
exo beta-D-galactofuranosidase
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 Penicillium fellutanum

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Penicillium fellutanum

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
4.6
-
 assay at Penicillium fellutanum