Selective α-glucosidase substrates and inhibitors containing short aromatic peptidyl moieties

Sangeun Park; Soonsil Hyun; Su-il Do; Jaehoon Yu

doi:10.1016/j.bmcl.2011.02.062

Selective α-glucosidase substrates and inhibitors containing short aromatic peptidyl moieties

Bioorg Med Chem Lett. 2011 Apr 15;21(8):2441-4. doi: 10.1016/j.bmcl.2011.02.062.

Authors

Sangeun Park¹, Soonsil Hyun, Su-il Do, Jaehoon Yu

Affiliation

¹ Department of Chemistry & Education, Seoul National University, Seoul 151-742, Republic of Korea.

PMID: 21397496
DOI: 10.1016/j.bmcl.2011.02.062

Abstract

We constructed a library of sugar-dipeptide conjugate to find out the best complementary against hydrophobic pocket of α-glucosidase. The best substrate showed 150-fold improved K(m) value relative p-acetaminophenyl-α-D-glucopyranoside for α-glucosidase from Bacillus stearothermophillus. Using information from the complementary, we synthesized sp-WY and β-Glc-sp-WY, which selectivity inhibited the cognate enzyme.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Bacillus / enzymology
Enzyme Inhibitors / chemical synthesis
Enzyme Inhibitors / chemistry*
Enzyme Inhibitors / pharmacology
Glycoside Hydrolase Inhibitors*
Hydrophobic and Hydrophilic Interactions
Oryza / enzymology
Peptides / chemical synthesis
Peptides / chemistry*
Peptides / pharmacology
Rats
Substrate Specificity
alpha-Glucosidases / metabolism

Substances

Enzyme Inhibitors
Glycoside Hydrolase Inhibitors
Peptides
alpha-Glucosidases