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Synthesis of New Photoactivatable Phenylalanine Analogues and Their Incorporation into a Model Peptide − Phenylseleno Derivatives as Precursors of α,β‐Unsaturated Ketones in Peptide Synthesis
Author(s) -
Jullian Valérie,
MonjardetBas Véronique,
Fosse Céline,
Lavielle Solange,
Chassaing Gérard
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200205)2002:10<1677::aid-ejoc1677>3.0.co;2-8
Subject(s) - moiety , chemistry , phenylalanine , ketone , peptide , peptide synthesis , stereochemistry , aqueous solution , combinatorial chemistry , organic chemistry , amino acid , biochemistry
The asymmetric synthesis of ( S )‐Boc‐ p ‐(propanoyl)phenylalanine ( 10 ) was performed by alkylation of sultam N ‐(diphenylmethylene)glycinate ( 4 ). Different pathways for the introduction of a phenylseleno moiety α to the ketone function were investigated. ( S )‐Boc‐ p ‐[2′‐(phenylselenenyl)propanoyl]phenylalanine ( 11 ) was easily obtained from ( S )‐Boc‐ p ‐(propanoyl)phenylalanine ( 10 ). However, the phenylseleno moiety α to the carbonyl group was found to be unstable to the conditions required for solid‐phase peptide synthesis. Therefore, (2 S )‐Boc‐ p ‐[2′‐(phenylselenenyl)propanoyl]phenylalanine ( 11 ) was transformed into Boc‐ p ‐[3′‐(phenylselenenyl)propanoyl]phenylalanine ( 13 ), which was successfully incorporated into the sequence of a model peptide. The corresponding enone function generated under mild acidic conditions was found to be stable in aqueous solution at pH = 7, but suitably reactive upon irradiation. Thus, these phenylalanine analogs bearing an unsaturated ketone represent new photoreactive probes. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)