Title: Synthesis and Stereoselective CC Bond‐forming Reactions of Peptide Aldehydes
Abstract: Liebigs AnnalenVolume 1996, Issue 3 p. 335-348 Full Paper Synthesis and Stereoselective CC Bond-forming Reactions of Peptide Aldehydes Manfred T. Reetz, Corresponding Author Manfred T. Reetz Max-Planck-Institut für Kohlenforschung Kaiser-Wilhelm-Platz 1, D-45470 Mülheim/Ruhr, Germany Telefax: (internat.) +49(0)2083062985 E-mail: [email protected]Max-Planck-Institut für Kohlenforschung Kaiser-Wilhelm-Platz 1, D-45470 Mülheim/Ruhr, Germany Telefax: (internat.) +49(0)2083062985 E-mail: [email protected]Search for more papers by this authorNils Griebenow, Nils Griebenow Max-Planck-Institut für Kohlenforschung Kaiser-Wilhelm-Platz 1, D-45470 Mülheim/Ruhr, Germany Telefax: (internat.) +49(0)2083062985 E-mail: [email protected]Search for more papers by this author Manfred T. Reetz, Corresponding Author Manfred T. Reetz Max-Planck-Institut für Kohlenforschung Kaiser-Wilhelm-Platz 1, D-45470 Mülheim/Ruhr, Germany Telefax: (internat.) +49(0)2083062985 E-mail: [email protected]Max-Planck-Institut für Kohlenforschung Kaiser-Wilhelm-Platz 1, D-45470 Mülheim/Ruhr, Germany Telefax: (internat.) +49(0)2083062985 E-mail: [email protected]Search for more papers by this authorNils Griebenow, Nils Griebenow Max-Planck-Institut für Kohlenforschung Kaiser-Wilhelm-Platz 1, D-45470 Mülheim/Ruhr, Germany Telefax: (internat.) +49(0)2083062985 E-mail: [email protected]Search for more papers by this author First published: March 1996 https://doi.org/10.1002/jlac.199619960308Citations: 8AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract The reaction of the activated form of N-protected amino acids 6 and 10 or peptides 14 and 18 with chiral amino alcohols derived from the corresponding α-amino acids affords peptide alcohols which can be oxidized under Swern conditions to produce the corresponding peptide aldehydes 9, 12, 16 and 20. The rational synthesis of diastereomeric di- and tripeptide aldehydes, e.g., (S,S)- or (R,S)-dipeptides as well as (S,S,S)- or (R,S,S)-tripeptides is possible by proper choice of the respective building blocks [(S)- versus (R)-amino acids]. The compounds can be prepared without any undesired α-epimerization. However, the long-term configurational stability depends upon the configuration at the remote stereogenic center, e.g., (R,S)-dipeptide aldehydes epimerize faster than the (S,S) diastereomers. Di- and tripeptide aldehydes 9, 12, 16 and 20 undergo chelation-controlled Grignard-type additions with Me2CuLi that involve little or no undesired α-epimerization. The (S,S)- and (R,S)-dipeptide aldehydes 9 and 12 undergo chelation-controlled pinacol reactions induced by the low-valent vanadium reagent [V2Cl3(THF)6]2[Zn2Cl6]. The major products in both cases are the corresponding C2-symmetric diols 33 and 36, respectively, which are of interest as potential HIV-protease inhibitors. The degree of stereoselectivity is significantly higher in the case of the (S,S)-dipeptide aldehydes relative to the (R,S) analogs, an observation which can be explained on the basis of three-point binding of the peptides to vanadium. References 1 [1a] T. Aoyagi, T. Takeuchi, A. Matsuzaki, M. Kawamura, M. Kondo, M. Hamada, K. Maeda, H. Umezawa, J. Antibiot. 1969, 22, 283. 10.7164/antibiotics.22.283 CASPubMedWeb of Science®Google Scholar [1b] T. Aoyagi, H. 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Publication Year: 1996
Publication Date: 1996-03-01
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 19
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