追求免疫学的有机合成：用于制备多抗原性前列腺癌疫苗的全乙酰化GM2糖基氨基酸的大规模合成。

Organic synthesis in pursuit of immunology: large-scale synthesis of peracetylated GM2 glycosylamino acid for preparation of a multiantigenic prostate cancer vaccine.

作者信息

Cho Young Shin, Wan Qian, Danishefsky Samuel J

机构信息

Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10021, USA.

出版信息

Bioorg Med Chem. 2005 Sep 1;13(17):5259-66. doi: 10.1016/j.bmc.2005.06.018.

DOI:10.1016/j.bmc.2005.06.018

PMID:16006132

Abstract

We describe herein the stereo-controlled, large-scale synthesis of peracetylated GM2 glycosylamino acid. Key features of the synthesis include a newly modified [1+3] coupling reaction and an olefin cross-metathesis-hydrogenation sequence. The GM2 glycosylamino acid is now ready for incorporation into a hexavalent prostate cancer vaccine construct.

摘要

我们在此描述了全乙酰化GM2糖基氨基酸的立体控制大规模合成。该合成的关键特征包括一种新修饰的[1+3]偶联反应以及烯烃交叉复分解-氢化序列。GM2糖基氨基酸现已准备好被纳入一种六价前列腺癌疫苗构建体中。