4-C-Me-DAB and 4-C-Me-LAB - enantiomeric alkyl-branched pyrrolidine iminosugars - are specific and potent α-glucosidase inhibitors; acetone as the sole protecting group.
4-C-Me-DAB and 4-C-Me-LAB - enantiomeric alkyl-branched pyrrolidine iminosugars - are specific and potent α-glucosidase inhibitors; acetone as the sole protecting group.
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DOI：
10.1016/j.tetlet.2010.10.173
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发表时间：
2011-01-12
影响因子：
1.8
通讯作者：
Fleet, George W. J.
中科院分区：
文献类型：
--
作者：
da Cruz, Filipa P.;Newberry, Scott;Jenkinson, Sarah F.;Wormald, Mark R.;Butters, Terry D.;Alonzi, Dominic S.;Nakagawa, Shinpei;Becq, Frederic;Norez, Caroline;Nash, Robert J.;Kato, Atsushi;Fleet, George W. J.
从l-红素内酯合成4-C-Me-DAB[1,4-二脱氧-1,4-亚胺-4- c -甲基-d-阿拉伯糖醇]和4-C-Me-LAB[从d-红素内酯]只需要一个丙酮保护基团。讨论了pH对4-C-Me-DAB[盐的pKa约为8.4]的NMR谱的影响，并说明了在分析耦合常数和化学位移时需要注意的问题。4-C-Me-DAB（对大鼠肠道蔗糖酶Ki 0.89 μM, IC50 0.41 μM）是一种竞争性α-葡萄糖苷酶抑制剂，而4-C-Me-LAB（对大鼠肠道蔗糖酶Ki 0.95 μM, IC50 0.66 μM）是一种非竞争性α-葡萄糖苷酶特异性有效抑制剂。给出了DAB、LAB、4-C-Me-DAB、4-C-Me-LAB和isoDAB（但不包括isoLAB）抑制α-葡萄糖苷酶的基本原理。两者都是内质网α-葡萄糖苷酶I和II的抑制剂。
The syntheses of 4-C-Me-DAB [1,4-dideoxy-1,4-imino-4-C-methyl-d-arabinitol] from l-erythronolactone and of 4-C-Me-LAB [from d-erythronolactone] require only a single acetonide protecting group. The effect of pH on the NMR spectra of 4-C-Me-DAB [pKa of the salt around 8.4] is discussed and illustrates the need for care in analysis of both coupling constants and chemical shift. 4-C-Me-DAB (for rat intestinal sucrase Ki 0.89 μM, IC50 0.41 μM) is a competitive - whereas 4-C-Me-LAB (for rat intestinal sucrase Ki 0.95 μM, IC50 0.66 μM) is a non-competitive - specific and potent α-glucosidase inhibitor. A rationale for the α-glucosidase inhibition by DAB, LAB, 4-C-Me-DAB, 4-C-Me-LAB, and isoDAB – but not isoLAB – is provided. Both are inhibitors of endoplasmic reticulum (ER) resident α-glucosidase I and II.
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影响因子：
1.8
作者：
Best, Daniel;Jenkinson, Sarah F.;Fleet, George W. J.
通讯作者：
Fleet, George W. J.
影响因子：
4
作者：
Ho, Ching-Wen;Popat, Shinde D.;Lin, Chun-Hung
通讯作者：
Lin, Chun-Hung
影响因子：
1.8
作者：
Hotchkiss, DJ;Jenkinson, SF;Fleet, GWJ
通讯作者：
Fleet, GWJ
影响因子：
1.8
作者：
Bell, AA;Pickering, L;Fleet, GWJ
通讯作者：
Fleet, GWJ
影响因子：
3.9
作者：
Fosgerau, K;Westergaard, N;Lundgren, K
通讯作者：
Lundgren, K