Welcome to LookChem.com Sign In|Join Free

Article Doi

The Allyl Group for Protection in Carbohydrate Chemistry. Part 19. The Coupling of Allyl 2,3-Di-O-methyl-4-O-(3,6-di-O-methyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside to Bovine Serum Albumin. Preparation of a Diagnostic Reagent for Antibodies to the Major Glycolipid of Mycobacterium...

DOI: 10.1039/P19870001165

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1165 - 1170 (1987)

Update date:2022-08-04

Topics:

Authors:

Gigg, JillGigg, Jill

Gigg, RoyGigg, Roy

Payne, SheilaPayne, Sheila

Conant, RobertConant, Robert

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P19870001165

Epoxidation of allyl 4-O-(2,4-di-O-benzyl-3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranoside and subsequent alkaline hydrolysis of the epoxide and hydrogenolysis of the benzyl groups gave 2',3'-dihydroxypropyl 2,3-di-O-methyl-4-O-(3,6-di-O-methyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside which was cleaved with sodium metaperiodate to give the corresponding formylmethyl glycoside.Two other routes to the latter compound, via allyl 2,3-di-O-methyl-4-O-(3,6-di-O-methyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside, were also developed.The formylmethyl glycoside was coupled to bovine serum albumin using 'reductive amination' in the presence of sodium cyanoborohydride to give a glycoconjugate useful for the serodiagnosis of antibodies to the major glycolipid of Mycobacterium leprae in the sera of leprosy patients. 5',6'-Dihydroxyhexyl and 10',11'-dihydroxyundecyl 3,6-di-O-methyl-β-D-glucopyranosides were also prepared as intermediates for the synthesis of the 4-formylbutyl and 9-formylnonyl glucosides respectively which are also suitable for coupling to bovine serum albumin by the 'reductive amination' technique.

View More

Products guided by the article

Product name:allyl 4-O-(2,4-di-O-p-methoxybenzyl-3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Cas No:112254-90-7

112254-90-7

R&D Labs maybe for 112254-90-7

Relevant to this article

Hot Product