SYNTHESIS AND COMPARATIVE CONFORMATIONAL ENERGETICS OF D-PHENYLALANYLSARCOSINE AND ITS CYCLIC DEHYDRATION PRODUCT, (R)-1-METHYL-3-(PHENYLMETHYL)-2,5-PIPERAZINEDIONE

Authors
SPEERS P CHAN C WILCOCK R DOUGLAS KT
Citation
P. Speers et al., SYNTHESIS AND COMPARATIVE CONFORMATIONAL ENERGETICS OF D-PHENYLALANYLSARCOSINE AND ITS CYCLIC DEHYDRATION PRODUCT, (R)-1-METHYL-3-(PHENYLMETHYL)-2,5-PIPERAZINEDIONE, Amino acids, 12(1), 1997, pp. 49-56
Citations number
9
Categorie Soggetti
Biology
Journal title
Amino acids → ACNP
ISSN journal
09394451
Volume
12
Issue
1
Year of publication
1997
Pages
49 - 56
Database
ISI
SICI code
0939-4451(1997)12:1<49:SACCEO>2.0.ZU;2-2
Abstract
Synthetic protocols are presented both for D-PheSar and the correpondi ng cyclised diketopiperazine, prepared from N-t-butoxycarbonyl-protect ed D-PheSar. Deprotection conditions could be manipulated to yield eit her D-Phenylalanylsarcosine or (R)-1-methyl-3-(phenylmethyl)-2,5-piper azinedione. Molecular modelling revealed several low energy conformers which contained a Z-peptide bond and which were readily amenable to c yclisation. Cyclisation was found by HPLC to be fastest in strongly ac idic conditions.