Tetrahedron

Effects of steric bulk and stereochemistry on the rates of diketopiperazine formation from N-aminoacyl-2, 2-dimethylthiazolidine-4-carboxamides (Dmt dipeptide …

GARY Suaifan, MF Mahon, T Arafat, MD Threadgill

Index: Suaifan, Ghadeer A.R.Y.; Mahon, Mary F.; Arafat, Tawfiq; Threadgill, Michael D. Tetrahedron, 2006 , vol. 62, # 48 p. 11245 - 11266

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Citation Number: 18

Abstract

A peptide-like self-immolative molecular clip is required for release of active drugs from prodrugs by endopeptidases. Upon cleavage from the carrier, this clip must collapse and release the drug rapidly. A series of aminoacyl-5, 5-dimethylthiaproline (Aaa-Dmt) N-(2-(4- nitrophenyl) ethyl) amides were designed. Boc-l-aminoacyl fluorides were coupled with R- DmtOH to give Boc-l-Aaa-R-DmtOH, which were converted to the Boc-l-Aaa-R-Dmt N-(2-( ...