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Synthesis of phosphine containing amino acids: Utilization of peptide synthesis in ligand design
Author(s) -
Agarkov Anton,
Greenfield Scott,
Xie Dejian,
Pawlick Robert,
Starkey Gale,
Gilbertson Scott R.
Publication year - 2005
Publication title -
peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.20395
Subject(s) - chemistry , phosphine , combinatorial chemistry , rational design , amino acid , alanine , peptide , ligand (biochemistry) , peptidomimetic , combinatorial synthesis , drug design , asymmetric hydrogenation , alkylation , enantioselective synthesis , catalysis , nanotechnology , organic chemistry , biochemistry , materials science , receptor
Abstract Combinatorial chemistry has recently burst on the scene as a valuable tool for the discovery of new drug candidates. The ability to synthesize hundreds of compounds for screening is a useful complement to rational drug design. There are many similarities between the design of new therapeutic agents and the development of new asymmetric ligands, the most important of which is the limitation of a rational design strategy. For this reason a program was begun that would allow the use of combinatorial technology in the development of new ligands for transition metal catalyzed asymmetric reactions. Because of the large number of catalytic reactions they are involved in the system was based around phosphine ligands. This paper reports the synthesis of phosphine derivatives of alanine, proline, and the aromatic amino acids tyrosine and hydroxyphenylglycine. Examples of the use of these amino acids in the synthesis of peptides possessing helical and β‐turn secondary structures are presented. Metal complexes of these peptide‐based ligands are used in hydrogenation and alkylation reactions. © 2005 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 84: 48–73, 2006 This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.com