Solid-phase synthesis of hydrogen-bond surrogate-derived α-helices
作者： Gianluca Dimartino , Deyun Wang , Ross N. Chapman , Paramjit S. Arora
DOI: 10.1021/OL0506516
关键词: Peptide sequence 、 Combinatorial chemistry 、 Stereochemistry 、 Chemistry 、 Solid-phase synthesis 、 Metathesis 、 Ring-opening metathesis polymerisation 、 Acyclic diene metathesis 、 Hydrogen bond 、 Catalysis 、 Salt metathesis reaction
摘要: This report describes the solid-phase synthesis of hydrogen-bond surrogate-derived artificial α-helices by a ring-closing metathesis reaction. From series catalysts evaluated for these helices, Hoveyda−Grubbs catalyst was found to afford high yields macrocycle irrespective peptide sequence.
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sci-hub.se 参考文章(22)
Helen E. Blackwell, Robert H. Grubbs, Highly Efficient Synthesis of Covalently Cross-Linked Peptide Helices by Ring-Closing Metathesis Angewandte Chemie International Edition. ,vol. 37, pp. 3281- 3284 ,(1998) , 10.1002/(SICI)1521-3773(19981217)37:23<3281::AID-ANIE3281>3.0.CO;2-V
Matthias Scholl, Sheng Ding, Choon Woo Lee, Robert H. Grubbs, Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands. Organic Letters. ,vol. 1, pp. 953- 956 ,(1999) , 10.1021/OL990909Q
Peter Schwab, Robert H. Grubbs, Joseph W. Ziller, Synthesis and Applications of RuCl2(CHR‘)(PR3)2: The Influence of the Alkylidene Moiety on Metathesis Activity Journal of the American Chemical Society. ,vol. 118, pp. 100- 110 ,(1996) , 10.1021/JA952676D
Bin Yang, Dongxiang Liu, Ziwei Huang, Synthesis and helical structure of lactam bridged BH3 peptides derived from pro-apoptotic Bcl-2 family proteins. Bioorganic & Medicinal Chemistry Letters. ,vol. 14, pp. 1403- 1406 ,(2004) , 10.1016/J.BMCL.2003.09.101
Martin J.I. Andrews, Alethea B. Tabor, Forming stable helical peptides using natural and artificial amino acids Tetrahedron. ,vol. 55, pp. 11711- 11743 ,(1999) , 10.1016/S0040-4020(99)00678-X
Loren D Walensky, Andrew L Kung, Iris Escher, Thomas J Malia, Scott Barbuto, Renee D Wright, Gerhard Wagner, Gregory L Verdine, Stanley J Korsmeyer, Activation of Apoptosis in Vivo by a Hydrocarbon-Stapled BH3 Helix Science. ,vol. 305, pp. 1466- 1470 ,(2004) , 10.1126/SCIENCE.1099191
Thomas R. Hoye, Brian M. Eklov, Troy D. Ryba, Mikhail Voloshin, Letitia J. Yao, No-D NMR (no-deuterium proton NMR) spectroscopy: a simple yet powerful method for analyzing reaction and reagent solutions. Organic Letters. ,vol. 6, pp. 953- 956 ,(2004) , 10.1021/OL049979+
Christian E. Schafmeister, Julia Po, Gregory L. Verdine, An All-Hydrocarbon Cross-Linking System for Enhancing the Helicity and Metabolic Stability of Peptides Journal of the American Chemical Society. ,vol. 122, pp. 5891- 5892 ,(2000) , 10.1021/JA000563A
ARTHUR M. FELIX, EDGAR P. HEIMER, CHING-TSO WANG, THEODORE J. LAMBROS, ALAIN FOURNIER, THOMAS F. MOWLES, SARAH MAINES, ROBERT M. CAMPBELL, BOGDA B. WEGRZYNSKI, VOLDEMAR TOOME, DAVID FRY, VINCENT S. MADISON, Synthesis, biological activity and conformational analysis of cyclic GRF analogs. International Journal of Peptide and Protein Research. ,vol. 32, pp. 441- 454 ,(2009) , 10.1111/J.1399-3011.1988.TB01375.X
George Osapay, John W. Taylor, Multicyclic polypeptide model compounds. 2. Synthesis and conformational properties of a highly .alpha.-helical uncosapeptide constrained by three side-chain to side-chain lactam bridges Journal of the American Chemical Society. ,vol. 114, pp. 6966- 6973 ,(1992) , 10.1021/JA00044A003