Stereospecific synthesis of methyl 2-amino-2-deoxy-(6S)-deuterio-α, β-d-glucopyranoside and methyl 2, 6-diamino-2, 6-dideoxy-(6R)-deuterio-α, β-d-glucopyranoside: Side chain conformations of the 2-amino-2-deoxy and 2, 6-diamino-2, 6-dideoxyglucopyranosides. (7th August 2017)

• Record Type: Journal Article
• Authors: Kato, Takayuki; Vasella, Andrea; Crich, David
• Is Part Of: Carbohydrate research. Volume 448(2017)
• Page Start: 10
• Page End: 17
• Publication Date: 2017-08-07
• Subjects: Side chain conformation -- Deuterium labelling -- Conformational analysis -- Aminosugars; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2017.05.015
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: The stereospecifically labeled 6-monodeuterio methyl 2, 6-diamino-2, 6-dideoxy-α- and β-d -glucopyranosides were synthesized with a view to determining their side chain conformations. NMR studies in D2 O at pH 5 and pH 11 reveal both anomers to adopt very predominantly the gt conformation consistent with the gauche conformation of 2-aminoethanol and its acetate salt. In contrast, as also revealed with the help of stereospecifically-labelled monodeuterio isotopomers, the methyl 2-amino-2-deoxy-α- and β-d -glucopyranosides are an approximately 1:1 mixture of gg and gt conformers as is found in glucopyranose itself. Graphical abstract: Highlights: Stereospecific deuterium labelling. Assignment of pro-R and pro-S hydrogens in side chain. Side chain conformation.