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Issue 15, 2020
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Synthesis and evaluation of Nα,Nε-diacetyl-l-lysine-inositol conjugates as cancer-selective probes for metabolic engineering of GPIs and GPI-anchored proteins

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Abstract

Two myo-inositol derivatives having an Nα,Nε-diacetyl-L-lysine (Ac2Lys) moiety linked to the inositol 1-O-position through a self-cleavable linker and a metabolically stable 2-azidoethyl group linked to the inositol 3-O- and 4-O-positions, respectively, were designed and synthesized. The Ac2Lys moiety blocking the inositol 1-O-position required for GPI biosynthesis was expected to be removable by a combination of two enzymes, histone deacetylase (HDAC) and cathepsin L (CTSL), abundantly expressed in cancer cells, but not in normal cells, to transform these inositol derivatives into biosynthetically useful products with a free 1-O-position. As a result, it was found that these inositol derivatives could be incorporated into the glycosylphosphatidylinositol (GPI) biosynthetic pathway by cancer cells, but not by normal cells, to express azide-labeled GPIs and GPI-anchored proteins on cell surfaces. Consequently, this study has established a novel strategy and new molecular tools for selective metabolic labeling of cancer cells, which should be useful for various biological studies and applications.

Graphical abstract: Synthesis and evaluation of Nα,Nε-diacetyl-l-lysine-inositol conjugates as cancer-selective probes for metabolic engineering of GPIs and GPI-anchored proteins

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Supplementary files

Article information


Submitted
14 Feb 2020
Accepted
27 Mar 2020
First published
27 Mar 2020

Org. Biomol. Chem., 2020,18, 2938-2948
Article type
Paper

Synthesis and evaluation of Nα,Nε-diacetyl-L-lysine-inositol conjugates as cancer-selective probes for metabolic engineering of GPIs and GPI-anchored proteins

M. Jaiswal, S. Zhu, W. Jiang and Z. Guo, Org. Biomol. Chem., 2020, 18, 2938
DOI: 10.1039/D0OB00333F

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