A chemoenzymatic approach toward the preparation of site-specific antibody-drug conjugates

被引：6

作者：

Cai, Xiaoqing

Janda, Kim D. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 23期

关键词：

Chemoenzymatic; Antibody-drug conjugates; N-Azidoacetylgalactosamine; Chemical synthesis; GLCNAC-MODIFIED PROTEINS; CANCER-THERAPY; TRASTUZUMAB EMTANSINE; CLICK CHEMISTRY; LIVING SYSTEMS; AZIDE-ALKYNE; GLYCANS; GLYCOPROTEOMICS; IDENTIFICATION; CYCLOADDITION;

D O I：

10.1016/j.tetlet.2014.12.025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient chemical synthesis of UDP-N-azidoacetylgalactosamine (UDP-GalNAz) is presented, while the value of this molecule was demonstrated through its attachment to an antibody Fc domain. Thus, the antibody was first degalactosylated, which was followed by loading of the UDP-GalNAz with a recombinant galactosyltransferase. This engineered Azide-Fc-N-glycan antibody was subsequently 'clicked' by a strain-promoted alkyne-azide cycloaddition reaction for site-specific attachment of a fluorescent probe. The principles detailed will allow for the facile preparation of chemically defined homogeneous antibody-drug conjugates (ADCs). (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：3172 / 3175

页数：4

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