Cyclic esters and cyclodepsipeptides derived from lactide and 2,5-morpholinediones.

ABSTRACT: The reaction between Bu(n)Li in benzene and the solid polystyrene support PS-C6H4CH2NH2 leads to a lithiated species that can be represented as PS-C6H4CH2NHLi(LiBu)x, where x approximately 4, which is active in the ring-opening of the cyclic esters L-lactide, rac-lactide, and 2,5-morpholinediones. With approximately 10 eq of these monomeric six-membered rings and with heating, cyclic esters (MeCHC(O)O)n and [MeCHC(O)OCHRC(NH)O]n are reversibly released to the solution. These have been characterized by electrospray ionization MS, and some small rings have been separated by gel-permeation chromatography. Addition of NaBPh4 to a heated benzene solution containing these rings preferentially removes the 18-membered rings from solution. For lactide this is shown to form the basis for chemical am

SUBMITTER: Chisholm MH 

PROVIDER: S-EPMC1622824 | biostudies-literature | 2006 Oct

REPOSITORIES: biostudies-literature