Synthesis and comparative conformational energetics of D-phenylalanylsarcosine and its cyclic dehydration product, (R)-1-methyl-3-(phenylmethyl)-2,5-piperazinedione |
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| Authors: | P Speers C Chan R Wilcock Prof K T Douglas |
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| Institution: | (1) Department of Pharmacy, University of Manchester, M13 9PL Manchester, UK |
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| Abstract: | Summary Synthetic protocols are presented both for D-PheSar and the corresponding cyclised diketopiperazine, prepared from N-t-butoxycarbonylprotected D-PheSar. Deprotection conditions could be manipulated to yield either D-Phenylalanylsarcosine or (R)-1-methyl-3-(phenylmethyl)-2,5-piperazinedione. Molecular modelling revealed several low energy conformers which contained a Z-peptide bond and which were readily amenable to cyclisation. Cyclisation was found by HPLC to be fastest in strongly acidic conditions.Abbreviation HBTU
o-Benzotriazolyl-tetramethyluronium hexafluorophosphate |
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| Keywords: | Amino acids Diketopiperazine Conformational analysis Sarcosine Acid cyclisation |
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