Dehydrooligopeptides. I. The Facile Coupling of α-Amino Acids with α-Dehydroamino Acids to Dehydrodipeptides

作者: Yasuchika Yonezawa , Chung-gi Shin , Yuji Ono , Juji Yoshimura

DOI: 10.1246/BCSJ.53.2905

关键词:

摘要: N-Cbz- or N-Tos-α-dehydroamino acid (DHA) and its ester were prepared by the condensation of 2-oxo carboxylic with benzyl carbamate p-toluenesulfonamide. Subsequently, N-protected DHA N-free thus obtained coupled several L-α-amino esters (Boc Cbz)-L-α-amino respectively usual peptide synthetic methods to give a number different types dehydrodipeptide. The configurations all new dehydrodipeptides shown have (Z)-geometry.

参考文章(7)
David G. Doherty, Josephine E. Tietzman, Max Bergmann, PEPTIDES OF DEHYDROGENATED AMINO ACIDS Journal of Biological Chemistry. ,vol. 147, pp. 617- 637 ,(1943) , 10.1016/S0021-9258(18)72358-2
Ananthachari Srinivasan, Robert W. Stephenson, Richard K. Olsen, Synthesis of dehydroalanine peptides from beta-chloroalanine peptide derivatives. Journal of Organic Chemistry. ,vol. 42, pp. 2253- 2256 ,(1977) , 10.1021/JO00433A014
Michael L. English, Charles H. Stammer, The enzyme stability of dehydropeptides Biochemical and Biophysical Research Communications. ,vol. 83, pp. 1464- 1467 ,(1978) , 10.1016/0006-291X(78)91385-2
Chung-gi Shin, Yasuchika Yonezawa, Kazuo Unoki, Juji Yoshimura, α,β-Unsaturated Carboxylic Acid Derivatives. XVII. The Facile Synthesis of Ethyl α-Azido-α-alkenoates and Reduction to Ethyl α-Amino-α-alkenoates Bulletin of the Chemical Society of Japan. ,vol. 52, pp. 1657- 1660 ,(1979) , 10.1246/BCSJ.52.1657
Chung Ch'i Shin, Mitsuo Masaki, Masaki Ohta, Synthesis of 3-isopropylidene-2,5-piperazinediones Journal of Organic Chemistry. ,vol. 32, pp. 1860- 1863 ,(1967) , 10.1021/JO01281A035
Yasuyuki SHIMOHIGASHI, Nobuo IZUMIYA, Chemistry of Peptides Containing Dehydroamino Acid, Especially AM-toxins Journal of Synthetic Organic Chemistry Japan. ,vol. 36, pp. 1023- 1038 ,(1978) , 10.5059/YUKIGOSEIKYOKAISHI.36.1023