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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.

ABSTRACT: The stereospecifically labeled 6-monodeuterio methyl 2,6-diamino-2,6-dideoxy-?- and ?- d-glucopyranosides were synthesized with a view to determining their side chain conformations. NMR studies in D2O 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-?- and ?- d-glucopyranosides are an approximately 1:1 mixture of gg and gt conformers as is found in glucopyranose itself.

SUBMITTER: Kato T

PROVIDER: S-EPMC5529286 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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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.

Kato Takayuki T Vasella Andrea A Crich David D

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 D2O 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]

PMID: 28554123

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