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一种全保护的内消旋二氨基庚二酸（DAP）的简便合成方法及其在制备亲脂性 N-酰基 iE-DAP 中的应用。

A facile synthesis of fully protected meso-diaminopimelic acid (DAP) and its application to the preparation of lipophilic N-acyl iE-DAP.

机构信息

Laboratory of Organic and Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan.

出版信息

Molecules. 2013 Jan 16;18(1):1162-73. doi: 10.3390/molecules18011162.

DOI:10.3390/molecules18011162
PMID:23325104
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6270281/
Abstract

Synthesis of beneficial protected meso-DAP 9 by cross metathesis of the Garner aldehyde-derived vinyl glycine 1b with protected allyl glycine 2 in the presence of Grubbs second-generation catalyst was performed. Preparation of lipophilic N-acyl iE-DAP as potent agonists of NOD 1-mediated immune response from 9 is described.

摘要

在 Grubbs 第二代催化剂的存在下，通过 Garner 醛衍生的乙烯基甘氨酸 1b 与保护的烯丙基甘氨酸 2 的交叉复分解反应，合成了有益的保护 meso-DAP9。描述了从 9 制备亲脂性 N-酰基 iE-DAP，作为 NOD1 介导的免疫反应的有效激动剂。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4b8/6270281/f64379f18105/molecules-18-01162-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4b8/6270281/fe6686f73f18/molecules-18-01162-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4b8/6270281/952b84a9eaa7/molecules-18-01162-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4b8/6270281/4481a4058688/molecules-18-01162-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4b8/6270281/f64379f18105/molecules-18-01162-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4b8/6270281/fe6686f73f18/molecules-18-01162-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4b8/6270281/952b84a9eaa7/molecules-18-01162-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4b8/6270281/4481a4058688/molecules-18-01162-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4b8/6270281/f64379f18105/molecules-18-01162-sch002.jpg

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Effect of positive charge in VIP 16gamma-glutamyl diamino derivatives on hVPAC1 and hVPAC2 receptor function.
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A straightforward stereoselective synthesis of meso-, (S,S)- and (R,R)-2,6-diaminopimelic acids from cis-1,4-diacetoxycyclohept-2-ene.由顺式-1,4-二乙酰氧基环庚-2-烯直接立体选择性合成内消旋-、(S,S)-和(R,R)-2,6-二氨基庚二酸。
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