Work

Solid-Phase Synthesis of a Thymidinyl Dipeptide Urea Library

Year: 2007

Type: article

Abstract: A thymidinyl dipeptide urea library with structural similarity to the nucleoside peptide class of antibiotics was designed and synthesized. To generate the library, a solid-phase synthesis was developed starting from 5'-azidothymidine attached to a polystyrene butyl diethylsilane (PS-DES) resin support. This study describes the prelibrary solid-phase synthesis development including maximum loading capacity optimization, selection of orthogonal functionalized side-chain protection strategies, synthesis of a 64-member test library, and optimization of the final cleavage step. Using the optimized procedures, we synthesized a 1000-member library in a 50 micromol quantity using IRORI-directed sorting technology in MiniKans, producing the target library in good yields and purity.

Source: Journal of Combinatorial Chemistry

DOI: 10.1021/cc060154w

Authors: Dianqing Sun, Richard E. Lee

Institution: University of Tennessee Health Science Center

Language: English

Topic: Chemical Synthesis and Analysis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funder: National Institute of Allergy and Infectious Diseases

Awards: Multi-Drug Resistant Tuberculosis Drugs: Targeting Cell Wall Synthetic Enzymes, G953877658