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 language | English |
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Journal | Carbohydrate Research |
Volume | 253 |
Pages (from-to) | 51-67 |
ISSN | 0008-6215 |
DOIs | |
Publication status | Published - 1994 |
Externally published | Yes |