Journal article
Conformational equilibria of 4-thiomaltose and nitrogen analogues of maltose in aqueous solutions
Department of Chemistry, Carlsberg Laboratory, Gamle Carlsberg Vej 10, DK-2500 , Copenhagen Valby , Denmark1
Department of Organic Chemistry, The Technical University of Denmark, DK-2800 , Lyngby , Denmark2
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&z.sbnd;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.
Language: | English |
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Year: | 1992 |
Pages: | 51-67 |
ISSN: | 1873426x and 00086215 |
Types: | Journal article |
DOI: | 10.1016/0008-6215(92)84233-I |