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Synthesis, stereochemistry and conformational properties of diastereomeric cyclic dipeptides containing tetrahydro‐1,4‐thiazine‐3,5‐dicarboxylic acid
Author(s) -
Paradisi Mario Paglialunga,
Zecchini Giampiero Pagani,
Torrini Ines,
Lucente Gino
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270627
Subject(s) - chemistry , diastereomer , thiazine , hydrogenolysis , stereochemistry , dicarboxylic acid , cyclic peptide , dipeptide , amino acid , peptide , organic chemistry , catalysis , biochemistry
The synthesis of linear dipeptides containing N ‐protected L‐phenylalanine and (3 R‐cis )‐tetrahydro‐1,4‐thiazine‐3,5‐dicarboxylic acid dialkyl diester residues is described. N ‐Deprotection of these dipeptides by hydrogenolysis on palladium afforded directly a mixture of cis and trans dioxopiperazines. The stereochemistry and the solution conformational properties of the cyclic dipeptides are determined.