New enzymatic synthesis of 6(3)-modified maltooligosaccharides and their inhibitory activities for human alpha-amylases.
Ten new 6(3)-modified maltopentaoses and tetraoses were synthesized by enzymatic reactions utilizing cyclodextrin glycosyltransferase (EC 2.4.1.19) and subsequent human salivary alpha-amylase (HSA) (EC 3.2.1.1). Among these compounds, alpha-D-glucopyranosyl-(1-->4)- alpha-D-glucopyranosyl-(1-->4)-(6-deoxy-alpha-D-glucopyranosyl)-(1-->4)- alpha-D-glucopyranosyl-(1-->4)-D-glucopyranose (11) and alpha-D-glucopyranosyl-(1-->4)-(6-deoxy-alpha-D-glucopyranosyl)-(1-->4)- alpha-D-glucopyranosyl-(1-->4)-D-glucopyranose (12) showed strong inhibitory activities for human pancreatic alpha-amylase (HPA) and HSA. The IC50 of 6(3)-deoxymaltopentaose 11 (8.0 x 10(-5) M for HPA, 1.0 x 10(-4) M for HSA) and 6(3)-deoxymaltotetraose 12 (2.0 x 10(-3) M for HPA, 2.0 x 10(-3) M for HSA) were lower than that of 6(3)-deoxymaltotriose [(6-deoxy-alpha-D-glucopyranosyl)-(1-->4)-alpha-D- glucopyranosyl-(1-->4)-D-glucopyranose 13; 2.0 x 10(-3) M for HPA, 4.2 x 10(-2) M for HSA].
Uchida
R
R
Research and Development Division, Kikkoman Corporation, Chiba, Japan.
Nasu
A
A
Tokutake
S
S
Kasai
K
K
Tobe
K
K
Yamaji
N
N
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D005964:Glucosyltransferases / Q000378:metabolism*; D006801:Humans; D007202:Indicators and Reagents; D007700:Kinetics; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000494:pharmacology*; D010179:Pancreas / Q000201:enzymology; D012463:Saliva / Q000201:enzymology; D013329:Structure-Activity Relationship; D000516:alpha-Amylases / Q000037:antagonists & inhibitors / Q000378:metabolism*
D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D009844:Oligosaccharides; C021705:maltooligosaccharides; D005964:Glucosyltransferases; C019963:cyclomaltodextrin glucanotransferase; D000516:alpha-Amylases