Synthesis of novel conjugates of a saccharide, amino acids, nucleobase and the evaluation of their cell compatibility.
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.
Department of Chemistry, Brandeis University, 415 South Street, MS015, Waltham, MA 02453, USA.
Dan
D
Yuan
Department of Chemistry, Brandeis University, 415 South Street, MS015, Waltham, MA 02453, USA.
Xuewen
X
Du
Department of Chemistry, Brandeis University, 415 South Street, MS015, Waltham, MA 02453, USA.
Junfeng
J
Shi
Department of Chemistry, Brandeis University, 415 South Street, MS015, Waltham, MA 02453, USA.
Ning
N
Zhou
Department of Chemistry, King Abdulaziz University, Jeddah, Saudi Arabia.
Abdulgader Ahmed
AA
Baoum
Department of Chemistry, Brandeis University, 415 South Street, MS015, Waltham, MA 02453, USA.
Bing
B
Xu
cell compatibility; nucleobase; peptides; saccharide