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Polylactones, 46. Telechelic polylactones having amino acid, dipeptide or penicilline endgroups via macrocyclic polymerization
Author(s) -
Kricheldorf Hans R.,
Hauser Karsten
Publication year - 1999
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/(sici)1521-3927(19990601)20:6<319::aid-marc319>3.0.co;2-f
Subject(s) - trifluoroacetic acid , dipeptide , racemization , cleavage (geology) , chemistry , polymerization , polymer chemistry , tin , amino acid , organic chemistry , materials science , polymer , biochemistry , fracture (geology) , composite material
Using 2‐stanna‐1,3‐dioxepane (DSDOP) as cyclic initiator either neat ε ‐caprolactone ( ε ‐CL) or mixtures of ε ‐CL and L ‐lactide were polymerized in bulk. The resulting tin‐containing macrocyclic polylactones were reacted with an excess of N ‐protected amino acid or dipeptide 4‐chlorothiophenyl esters. It was shown that the coupling of amino acid thioaryl esters and tin‐containing macrocycles does not involve any racemization. The cleavage of Boc groups with trifluoroacetic acid proved to be feasible but not the hydrogenolytic cleavage of the Z‐group.