Biomaterial Database

Synthesis of 4-deoxy-D-xylo-hexose and 4-azido-4-deoxy-D-glucose and their effects on lactose synthase. 1980

S K Sinha, and K Brew

Syntheses are reported of 4-deoxy-D-xylo-hexose and 4-azido-4-deoxy-D-glucose as potential inhibitors for lactose synthase [uridine 5'-(alpha-D-galactopyranosyl pyrophosphate):D-glucose 4-beta-D-galactopyranosyltransferase, EC 2.4.1.22]. These syntheses involved SN2 displacement of the 4-methylsulfonyloxy group of methyl 2,3,6-tri-O-benzoyl-4-O-methylsulfonyl-alpha-D-galactopyranoside by iodide and azide ions. In both cases, inversion in configuration was observed. The resulting intermediates, methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-iodo-alpha-D-glucopyranoside and methyl 4-azido-2,3,6-tri-O-benzoyl-4-deoxy-alpha-D-glucopyranoside, were obtained in crystalline form. Both 4-deoxy-D-xylo-hexose and 4-azido-4-deoxy-D-glucose were found to be inhibitors for lactose synthase in the presence of alpha-lactalbumin, but had no effect in the absence of alpha-lactalbumin. Both D-glucose analogues bind to the enzyme system far more weakly than D-glucose, suggesting that the recognition of the 4-OH group of the acceptor substrate is an important factor in binding.

UI	MeSH Term	Description	Entries
D007700	Kinetics	The rate dynamics in chemical or physical systems.
D007788	Lactose Synthase	An enzyme complex that catalyzes the transfer of GALACTOSE from UDP GALACTOSE to GLUCOSE, forming LACTOSE. The enzyme complex is composed of a B subunit, ALPHA-LACTALBUMIN, which changes the substrate specificity of the A subunit, N-ACETYLLACTOSAMINE SYNTHASE, from N-ACETYLGLUCOSAMINE to glucose making lactose synthesis the preferred reaction.	Lactose Synthetase,N-Acetylgucosamide 1-4 beta Galactosyl Transferase,N Acetylgucosamide 1 4 beta Galactosyl Transferase,Synthase, Lactose,Synthetase, Lactose
D008722	Methods	A series of steps taken in order to conduct research.	Techniques,Methodological Studies,Methodological Study,Procedures,Studies, Methodological,Study, Methodological,Method,Procedure,Technique
D011247	Pregnancy	The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	Gestation,Pregnancies
D002417	Cattle	Domesticated bovine animals of the genus Bos, usually kept on a farm or ranch and used for the production of meat or dairy products or for heavy labor.	Beef Cow,Bos grunniens,Bos indicus,Bos indicus Cattle,Bos taurus,Cow,Cow, Domestic,Dairy Cow,Holstein Cow,Indicine Cattle,Taurine Cattle,Taurus Cattle,Yak,Zebu,Beef Cows,Bos indicus Cattles,Cattle, Bos indicus,Cattle, Indicine,Cattle, Taurine,Cattle, Taurus,Cattles, Bos indicus,Cattles, Indicine,Cattles, Taurine,Cattles, Taurus,Cow, Beef,Cow, Dairy,Cow, Holstein,Cows,Dairy Cows,Domestic Cow,Domestic Cows,Indicine Cattles,Taurine Cattles,Taurus Cattles,Yaks,Zebus
D003126	Colostrum	The thin, yellow, serous fluid secreted by the mammary glands during pregnancy and immediately postpartum before lactation begins. It consists of immunologically active substances, white blood cells, water, protein, fat, and carbohydrates.	Colostrums
D003837	Deoxy Sugars	Sugars that in which one or more hydroxyl groups of the pyranose or furanose ring is substituted by hydrogen.	Deoxy Sugar,Sugar, Deoxy,Sugars, Deoxy
D003847	Deoxyglucose	2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.	2-Deoxy-D-glucose,2-Deoxyglucose,2-Desoxy-D-glucose,2 Deoxy D glucose,2 Deoxyglucose,2 Desoxy D glucose
D005260	Female		Females
D005700	Galactosyltransferases	Enzymes that catalyze the transfer of galactose from a nucleoside diphosphate galactose to an acceptor molecule which is frequently another carbohydrate. EC 2.4.1.-.	Galactosyltransferase