Bock K, Duus J O, Refn S
Department of Chemistry, Carlsberg Laboratory, Copenhagen Valby.
Carbohydr Res. 1994 Feb 3;253:51-67. doi: 10.1016/0008-6215(94)80055-3.
The 1H and 13C NMR data at neutral pH are presented for methyl 4-thio-beta- and alpha-maltoside (1 and 2) together with methyl 1-thio-alpha-D-glucopyranoside (3) and methyl 4-thio-alpha-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 alpha-maltoside (5 and 6) and the 5-amino-5-deoxy analogue (8) together with reference compounds methyl 4-amino-4-deoxy-alpha-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 alpha- and beta-maltoside and the results discussed in light of earlier studies.
给出了中性pH条件下4-硫代-β-和α-麦芽糖甲基苷（1和2）以及作为参考化合物的1-硫代-α-D-吡喃葡萄糖苷甲基苷（3）和4-硫代-α-D-吡喃葡萄糖苷甲基苷（4）的¹H和¹³C NMR数据。此外，还给出了α-麦芽糖甲基苷（5和6）的4-氨基-4-脱氧类似物和5-氨基-5-脱氧类似物（8）以及参考化合物4-氨基-4-脱氧-α-D-吡喃葡萄糖苷甲基苷（7）和1-脱氧野尻霉素（9）在高pH和低pH条件下的NMR数据。实验NMR数据通过500和600 MHz的一维和二维光谱进行归属。通过差异NOE实验、¹³C-¹H远程耦合常数、与模型化合物的化学位移比较以及使用蒙特卡罗模拟对1进行硬球力场计算，评估了麦芽糖类似物1、2、5、6和8的构象偏好。此外，将结果与α-和β-麦芽糖甲基苷的大量实验NOE数据进行了比较，并根据早期研究对结果进行了讨论。
