ABSTRACT
4P-X (ß-D-galactopyranosyl-(1 â 4)-ß-D-galactopyranosyl-(1 â 6)-[ß-D-galactopyranosyl-(1 â 4)]-ß-D-glucopyranose) is included in galacto-oligosaccharides (GOSs) produced by ß-galactosidase derived from Bacillus circulans. 4P-X has been known to induce particularly strong allergies. High purity 4P-X is essential for use as a standard to quantify the amount of 4P-X in GOSs; however, the isolation of high purity 4P-X has never been reported. In this study, we achieved the synthesis of 4P-X by a combination of organic and enzymatic chemical syntheses in a short time. This is the first report of isolated, high purity 4P-X.
Subject(s)
Bacterial Proteins/chemistry , Galactose/chemistry , Oligosaccharides/chemical synthesis , Oligosaccharides/isolation & purification , beta-Galactosidase/chemistry , Bacillus/chemistry , Bacillus/enzymology , Disaccharides/chemistry , Humans , Hypersensitivity/etiology , Hypersensitivity/immunology , Lactose/chemistry , Oligosaccharides/pharmacologyABSTRACT
The organ selectivity and the effect on myocardial ischemia-reperfusion injury of (R)-acetoxyhexamide ((R)-ACX), a novel sulfonylurea, were examined. (R)-ACX, as well as glibenclamide, concentration-dependently stimulated insulin release from INS-1 cell, a cell line derived from pancreatic beta-cells. The potency of (R)-ACX was about 1/10 of that of glibenclamide. In isolated guinea pig ventricular myocardial tissue, glibenclamide concentration-dependently inhibited the action potential shortening by NIP-121, an ATP-sensitive potassium channel opener, but (R)-ACX showed only slight inhibition. In isolated rat aortic rings contracted with norepinephrine, glibenclamide concentration-dependently inhibited the relaxation by NIP-121, while (R)-ACX showed only slight inhibition. In coronary-perfused guinea pig ventricular preparations, glibenclamide reduced the recovery of contractile force after ischemia-reperfusion, while (R)-ACX did not. In conclusion, (R)-ACX is a beta-cell selective sulfonylurea which, unlike glibenclamide, does not aggravate cardiac ischemia-reperfusion damage.
Subject(s)
Insulin-Secreting Cells/drug effects , Myocardial Reperfusion Injury/physiopathology , Sulfonylurea Compounds/pharmacology , Action Potentials/drug effects , Animals , Benzopyrans/pharmacology , Cells, Cultured , Female , Glyburide/pharmacology , Glyburide/toxicity , Guinea Pigs , Hypoglycemic Agents/pharmacology , Hypoglycemic Agents/toxicity , In Vitro Techniques , Male , Muscle Relaxation/drug effects , Muscle, Smooth, Vascular/drug effects , Myocardial Contraction/drug effects , Papillary Muscles/drug effects , RatsABSTRACT
Enzymatic glycosidation of twenty-one kinds of alcohols (n-hepanol, n-octanol, 2-phenylethanol, 3-phenylpropanol, 4-phenylbutanol, 5-phenylpentanol, 6-phenylhexanol, furfury alcohol, 2-pyridinemethanol, isobutanol, isopentanol, p-methoxycinnamylalcohol) including secondary alcohols (isopropanol, cyclohexanol, 1-phenylethanol) and 1,omega-alkanediols (1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol), salicyl alcohol and 4-nitrophenyl beta-D-glucopyranoside (5) using beta-glucosidase from almonds stereoselectively gave the corresponding beta-D-glucopyranosides in moderate yield.
