Depsipeptide dendrimers

Chemistry : a European Journal
J KressA Hirsch

Abstract

The convergent synthesis of a new class of chiral dendrimers is described. Owing to their structural resemblance to depsipeptides they are called depsipeptide dendrimers. The ex-chiral pool synthesis starts from (R,R)-, (S,S)-, and meso-tartaric acid as branching units and dipeptides or tripeptides consisting of glycine, (L)-alanine, and (L)-leucine as chiral-spacer building blocks. The key intermediates for the convergent assembly of such depsipeptide dendrimers are the peptide-tartaric acid conjugates 13a,b, 19a,b, 25, and 27, which contain either an unprotected C terminus of the peptide chain (13 a,b, 25) or two unprotected hydroxy groups within the tartaric acid termini. Dendra up to the third-generation, by using different combinations of stereoisomeric building blocks, were synthesized and completely characterized. Since this construction principle of chiral depsipeptide dendrimers allows for a wide variation of the length, the primary structure of the peptide spacer, and the configuration of both the amino acid and the tartaric acid moieties, access to new combinatorial libraries is conceptually provided.

Citations

Dec 5, 2013·Pharmaceutical Development and Technology·Rahul S KalhapureThirumala Govender
Mar 12, 2010·Pharmaceuticals·Colin V Bonduelle, Elizabeth R Gillies
Apr 7, 2005·Chemistry : a European Journal·Boris BuschhausAndreas Hirsch
Feb 24, 2006·Chemistry : a European Journal·Kristine HagerAndreas Hirsch
Feb 20, 2008·Chemical Communications : Chem Comm·Susan E Gibson, Jacob T Rendell
Dec 13, 2001·Chemical Reviews·S M Grayson, J M Fréchet
Jun 19, 2009·Chemical Reviews·Scott H Medina, Mohamed E H El-Sayed
May 12, 2005·Chemical Reviews·Laia CrespoFernando Albericio
Sep 18, 2001·The Journal of Organic Chemistry·M J LaufersweilerJ R Parquette
Sep 27, 2019·Chemical Reviews·Rachit SapraV Haridas
Jul 26, 2002·Journal of the American Chemical Society·Laia CrespoErnest Giralt
Feb 12, 2005·Organic Letters·Fernando AlbericioJan Spengler

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