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Beilstein J Org Chem. 2014 Oct 16;10:2406-13. doi: 10.3762/bjoc.10.250. eCollection 2014.

Synthesis of novel conjugates of a saccharide, amino acids, nucleobase and the evaluation of their cell compatibility.

Author information

1
Department of Chemistry, Brandeis University, 415 South Street, MS015, Waltham, MA 02453, USA.
2
Department of Chemistry, King Abdulaziz University, Jeddah, Saudi Arabia.

Abstract

This article reports the synthesis of a novel type of conjugate of three fundamental biological build blocks (i.e., saccharide, amino acids, and nucleobase) and their cell compatibility. The facile synthesis starts with the synthesis of nucleobase and saccharide derivatives, then uses solid-phase peptide synthesis (SPPS) to build the peptide segment (Phe-Arg-Gly-Asp or naphthAla-Phe-Arg-Gly-Asp with fully protected groups), and later, an amidation reaction in liquid phase connects these three parts together. The overall yield of these multiple step synthesis is about 34%. Besides exhibiting excellent solubility, these conjugates of saccharide-amino acids-nucleobase (SAN), like the previously reported conjugates of nucleobase-amino acids-saccharide (NAS) and nucleobase-saccharide-amino acids (NSA), are mammalian cell compatible.

KEYWORDS:

cell compatibility; nucleobase; peptides; saccharide

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