Dataset Information
Stereospecific synthesis of methyl 2-amino-2-deoxy-(6S)-deuterio-?,?-d-glucopyranoside and methyl 2,6-diamino-2,6-dideoxy-(6R)-deuterio-?,?-d-glucopyranoside: Side chain conformations of the 2-amino-2-deoxy and 2,6-diamino-2,6-dideoxyglucopyranosides.
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ABSTRACT:
SUBMITTER: Kato T
PROVIDER: S-EPMC5529286 | biostudies-literature | 2017 Aug
REPOSITORIES: biostudies-literature
Publications
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.
Carbohydrate research 20170519
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 D<sub>2</sub>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- ...[more]