Allyl side chain protection in peptide synthesis
作者： Derek Hudson , Matthew H. Lyttle
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摘要: A system for the protection of amino acid side-chain functional moieties during peptide synthesis, comprising use allyl protecting groups, such as, example, ether, ester, thioether allyloxycarbonyl and allyloxymethyl groups. The present groups do not exert adverse steric effects on bond condensation, are fully orthogonal to a variety popular αN-protecting including Fmoc tBoc. Moreover, deprotection is mild, does result in formation reactive carbonium ions. Allyl can be used alone or conjunction with other types
lens.org 参考文章(9)
Hai Zhang, Albert Loffet, Method for synthesizing peptides, novel amino acid derivatives used therein, and methods for preparing same. ,(1992)
Thomas Gadek, John P. Burnier, Eugene D. Thorsett, Peter L. Barker, Small cyclic platelet aggregation inhibitors. ,(1990)
Ichiro Minami, Masami Yuhara, Jiro Tsuji, 1-Isopropylallyloxycarbonyl (IPAoc) as a protective group of amines and its deprotection catalysed by palladium-phosphine complex Tetrahedron Letters. ,vol. 28, pp. 2737- 2740 ,(1987) , 10.1016/S0040-4039(00)96195-1
Guillermo Tous, Andrew Bush, Ana Tous, Frank Jordan, O'-(epoxyalkyl)tyrosines and (epoxyalkyl)phenylalanine as irreversible inactivators of serine proteases: synthesis and inhibition mechanism. Journal of Medicinal Chemistry. ,vol. 33, pp. 1620- 1634 ,(1990) , 10.1021/JM00168A015
O. Dangles, F. Guibe, G. Balavoine, S. Lavielle, A. Marquet, Selective cleavage of the allyl and (allyloxy)carbonyl groups through palladium-catalyzed hydrostannolysis with tributyltin hydride. Application to the selective protection-deprotection of amino acid derivatives and in peptide synthesis Journal of Organic Chemistry. ,vol. 52, pp. 4984- 4993 ,(1987) , 10.1021/JO00231A027
Peter J. Belshaw, Shadreck Mzengeza, Gilles A. Lajoie, Chlorotrimethylsilane Mediated Formation of ω-Allyl Esters of Aspartic And Glutamic Acids Synthetic Communications. ,vol. 20, pp. 3157- 3160 ,(1990) , 10.1080/00397919008051540
F Guibe, O Dangles, G Balavoine, Palladium-catalyzed reaction of tributyltin hydride. Selective and very mild deprotection of allyl and allyloxycarbonyl derivatives of amino-acids Tetrahedron Letters. ,vol. 27, pp. 2365- 2368 ,(1986) , 10.1016/S0040-4039(00)84530-X
M. MANIKOSHI, B. KUNDU, K. L. RINEHART, Use of Tetrabutylammonium Fluoride as a Facile Deprotecting Reagent for 4-Nitrobenzyl, 2,2,2-Trichloroethyl, and Phenacyl Esters of Amino Acids. ChemInform. ,vol. 23, ,(2010) , 10.1002/CHIN.199211101
Carl M. Stevens, Ronald Watanabe, Amino Acid Derivatives. I. Carboallyloxy Derivatives of α-Amino Acids1,2 Journal of the American Chemical Society. ,vol. 72, pp. 725- 727 ,(1950) , 10.1021/JA01158A020