Enzymatic synthesis of a new inhibitor of alpha-amylases: acarviosinyl-isomaltosyl-spiro-thiohydantoin.
Synthesis of acarviosinyl-isomaltosyl-spiro-thiohydantoin in yields up to 20%, has been achieved by Bacillus stearothermophilus maltogenic amylase (BSMA). BSMA is capable of transferring the acarviosine-glucose residue from an acarbose donor onto glucopyranosylidene-spiro-thiohydantoin. Reactions were followed using HPLC and MALDI-TOF MS. 1H and 13C NMR studies revealed that the enzyme reserved its stereoselectivity. Glycosylation took place mainly at C-6 resulting in alpha-acarviosinyl-(1-->4)-alpha-D-glucopyranosyl-(1-->6)-D-glucopyranosylidene-spiro-thiohydantoin. This compound was found to be a much more efficient salivary amylase inhibitor than glucopyranosylidene-spiro-thiohydantoin with kinetic constants of K(EI)=0.19 microM and K(ESI)=0.24 microM.
Kandra
Lili
L
Department of Biochemistry, Faculty of Sciences, University of Debrecen, PO Box 55, 4010 Debrecen, Hungary. kandra@tigris.klte.hu
Remenyik
Judit
J
Batta
Gyula
G
Somsák
László
L
Gyémánt
Gyöngyi
G
Park
Kwan Hwa
KH
D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000378:metabolism; D001411:Geobacillus stearothermophilus / Q000201:enzymology*; D006026:Glycoside Hydrolases / Q000737:chemistry*; D009844:Oligosaccharides / Q000096:biosynthesis* / Q000737:chemistry; D013867:Thiohydantoins / Q000737:chemistry; D000516:alpha-Amylases / Q000037:antagonists & inhibitors*
D004791:Enzyme Inhibitors; D009844:Oligosaccharides; D013867:Thiohydantoins; C504162:acarviosinyl-isomaltosyl-spiro-thiohydantoin; D006026:Glycoside Hydrolases; D000516:alpha-Amylases; C120909:glucan 1,4-alpha-maltohydrolase