Conformational equilibria of 4-thiomaltose and nitrogen analogues of maltose in aqueous solutions

Klaus Bock, Jens Øllgaard Duus, Susanne Refn

Research output: Contribution to journalJournal articlepeer-review

Abstract

The 1H and 13C NMR data at neutral pH are presented for methyl 4-thio-β- and α-maltoside (1 and 2) together with methyl 1-thio-α-d-glucopyranoside (3) and methyl 4-thio-α-d-glucopyranoside (4) as reference compounds. Furthermore, the NMR data at high and low pH are presented for the 4-amino-4-deoxy analogues of methyl α-maltoside (5 and 6) and the 5-amino-5-deoxy analogue (8) together with reference compounds methyl 4-amino-4-deoxy-α-d-glucopyranoside (7) and 1-deoxynojirimycin (9). The experimental NMR data are assigned by 1- and 2-dimensional spectroscopy at 500 and 600 MHz. The conformational preferences of the maltose analogues 1, 2, 5, 6 and 8 are evaluated by difference NOE experiments, 13C-1H long-range coupling constants, chemical-shift comparison with model compounds and hard-sphere force field calculations for 1 using Monte Carlo simulations. Additionally, the results are compared with extensive experimental NOE data for methyl α- and β-maltoside and the results discussed in light of earlier studies.
Original languageEnglish
JournalCarbohydrate Research
Volume253
Pages (from-to)51-67
ISSN0008-6215
DOIs
Publication statusPublished - 1994
Externally publishedYes

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