Full-Text Search:
Home|Journal Papers|About CNKI|User Service|FAQ|Contact Us|中文
《Acta Chimica Sinica》 1966-01
Add to Favorite Get Latest Update

CYSTEINE PEPTIDES——III. SYNTHESIS OF A PROTECTED N-TERMINAL NONAPEPTIDE OF THE A-CHAIN OF BOVINE INSULIN

WANG Yu; CHI Ai-Hsueh; LOH Teh-Pei; LI Chung-Hsi; SHI Pu-Tao; YIEH Yuen-Hwa; TANG Car-Lo; HSING Chi-Yi Department of Chemistry, Peking University Institute of Organic Chemistry, Academia Sinica  
The synthesis of a protected N-terminal nonapeptide of the A-chain of bovine insulin N-carbobenzoxy-glycyl-L-leucyl-L-valyl-γ-t-butyl-glutaminyl-S-benzyl-L-cysteinyl-S-benzyl-L-cysteinyl-L-alanyl-O-acetyl-L-serine (IIa) and its methyl ester (I) and hydrazide (II) are described. Nonapeptide I was synthesized by the condensation of N-deblocked N-carbobenzoxy-L-glutaminyl-S-benzyl-L-cysteinyl-S-benzyl-L-cysteinyl-L-alanyl-O-acetyl-L-serine methyl ester (V) either with N-carbobenzoxy-glycyl-L-isoleucyl-L-valyl-γ-t-butyl-L-glutamic acid (IVa) through the N,N'-dicyclohexylcarbodiimide method or with hydrazide IV through the azide method. Hydrazinolysis and saponification of peptide I gave the corresponding peptide derivatives II and IIa. Tetrapeptide IVa and its hydrazide IV were obtained from the corresponding tetrapeptide cthyl ester III. Tetrapeptide III was obtained either by the condensation of N-deblocked N-carbobenzoxy-L-valyl-γ-t-butyl-L-glutamate ethyl ester with N-carbobenzoxy-glycyl-L-isoleucyl hydrazide (VII) through the azide method or by condensation of N-carbobenzoxy-glycyl-L-isoleucyl-L-valine (VIII) with γ-t-butyl-L-glutamate ethyl ester (IX) through the N,N'-dicyclohexylcarbodiimide method. Pentapeptide V was synthesized by coupling N-carbobenzoxy-L-glutamine-p-nitrophenyl ester (XIII) with either the known tetrapeptide N-carbobenzoxy-S-benzyl-L-cysteinyl-S-benzyl-L-cyteinyl-L-alanyl-L-serine methyl ester (XIIa) or with N-carbobenzoxy-S-benzyl-L-cysteinyl-S-benzyl-L-cysteinyl-L-alanyl-O-acetyl-L-serine methyl ester (XII) after N-decarbobenzoxylation by hydrogen bromide in glacial acetic acid. Va was obtained if XIIa was first N-decarbobenzoxylated by hydrogen bromide in trifluoroacitic acid and then coupled with XIII. Va was also obtained by condensation of the known peptide N-carbobenzoxy-L-glutaminyl-S-benzyl-L-cyteinyl-S-benzyl-L-cysteinyl hydrazide (XIV) with L-alanyl-L-serine methyl ester (X) through the azide method. Results from elementary analyses, paper chromatography, paper electrophoresis and amino acid analysis indicated that peptide I was analytically pure. It is very probably that peptide I is an optically homogeneous compound, since both the azide and the carbodiimide methods gave the same product.
Download(CAJ format) Download(PDF format)
CAJViewer7.0 supports all the CNKI file formats; AdobeReader only supports the PDF format.
【Co-references】
Chinese Journal Full-text Database 5 Hits
1 WANG YU, HSU JE-ZEN, LOH JEN-YUNG, HUANG KANG~* AND HUANG JING-JAIN(Institute of Organic Chemistry, Academia Sinica);STUDIES ON PEPTIDES Ⅰ. SYNTHESIS OF PROTECTED N-TERMINAL PENTAPEPTIDES OF THE A-CHAIN OF INSULIN[J];Acta Chimica Sinica;1963-02
2 LI CHUNG-HSI, LOH TEH-PEI, CHANG MING-CHE, WU SHAO-LAN AND HSING CHI-YI(Division of Organic Chemistry, Chemistry Department, Peking University);CYSTEINE PEPTIDES Ⅰ. SYNTHESIS OF A PROTECTED HEXAPEPTIDE WITH THE AMINOACID SEQUENCE 6—11 OF THE A-CHAIN OF INSULIN[J];Acta Chimica Sinica;1963-02
3 WANG YU, TU CHUAN-TSUNG, LOH HSI-YIEN, CHANG WEI-CHUN,WANG CHIK-CHIN, CHEN YOH-CHONG AND TANG YUNG-TI(Institute of Organic Chemistry, Academia Sinica);STUDIES ON PEPTIDES Ⅳ. SYNTHESIS OF PROTECTED C-TERMINAL DODEDECA- AND HEXADECAPEPTIDE OF THE A-CHAIN OF BOVINE INSULIN[J];Acta Chimica Sinica;1964-02
4 LOH TEH-PEI, LI CHUNG-HSI AND HSING CHI-YI (Department of Chemistry, Peking University);CYSTEINE PEPTIDES Ⅱ. AN IMPROVED SYNTHESIS OF PROTECTED HEXAPEPTIDE WITH THE AMINO ACID SEQUENCE 6—11 OF THE A-CHAIN OF INSULIN AND ITS ANALOGUES[J];Acta Chimica Sinica;1965-06
5 SHIEH SHER-PU;PU I-SEN Department of Experimental Morphology,Chinese Academy of Medical Sciences,Peking;AN AUTORADIOGRAPHIC STUDY ON THE UPTAKE OF RADIOSULPHATE (S~(35))——METHIONINE IN THE EMBRYONIC TISSUE VERSUS YOLK MATERIAL OF THE DEVELOPING CHICK EMBRYO[J];Acta Anatomica Sinica;1958-02
【Secondary References】
Chinese Journal Full-text Database 5 Hits
1 Ye Weixin (Toregji Medical University);The present situation and development on the research of radioimmunoassay methodology[J];Nuclear Techniques;1987-07
2 Wang Shizhen (Shih-Chen Wang) (Capital Nuclear Medicine Center, CAMS);Nuclear medicine in China: Present status and future trends[J];Nuclear Techniques;1988-10
3 HUANG Tiansen (Shanghai Institute of Drug Control, Shanghai 200233);Formation and development in control cause of radiopharmaceuticals of China[J];Nuclear Techniques;1999-05
4 Ma Chongzhi (China Institute of Atumic Energy, Beijing 102413);SURVEY OF RADIOPHARMACEUTICAL DEVELOPMENT[J];Journal of Isotopes;1992-03
5 XIA Zheng-min, ZHONG Jian-guo (The National Institute for the Control of Pharmaceuticals and Biological Products, Beijing 100050, China);The Brief Introduction of the History of Radiopharmaceuticals in China[J];Journal of Isotopes;2002-02
©2006 Tsinghua Tongfang Knowledge Network Technology Co., Ltd.(Beijing)(TTKN) All rights reserved