SYNTHETIC STUDY ON PEPTIDE ANTIBIOTIC NISIN .5. TOTAL SYNTHESIS OF NISIN

被引：59

作者：

FUKASE, K ^{[1
]}

KITAZAWA, M ^{[1
]}

SANO, A ^{[1
]}

SHIMBO, K ^{[1
]}

HORIMOTO, S ^{[1
]}

FUJITA, H ^{[1
]}

KUBO, A ^{[1
]}

WAKAMIYA, T ^{[1
]}

SHIBA, T ^{[1
]}

机构：

[1] OSAKA UNIV, FAC SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1992年 / 65卷 / 08期

关键词：

D O I：

10.1246/bcsj.65.2227

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Total synthesis of a lanthionine peptide nisin was achieved by the successive condensations of four segments including cyclic lanthionine peptide parts and the C-terminal linear segment including dehydroalanine, followed by the deprotection procedure with anhydrous HF. Modified reaction conditions for the Hofmann degradation were applied to prepare the dehydroalanine residue from the 2,3-diaminopropionic acid residue. The final deprotection with anhydrous HF proceeded without decomposition of the dehydroamino acid residues which are generally labile in acidic media. The synthetic nisin was completely identical with the natural one in all respects, resulting in a confirmation of the proposed structure.

引用

页码：2227 / 2240

页数：14

共 50 条

[1] SYNTHESIS OF CYCLO-DIGLYCYL-L-LYSYL-DIGLYCYL-L-LYSYL AND HYDROLYSIS BY TRYPSIN [J].

ABE, O ;

TAKIGUCHI, H ;

OHNO, M ;

MAKISUMI, S ;

IZUMIYA, N .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1967, 40 (08) :1945-+

[2]

ANDERSEN AA, 1953, ANTIBIOT CHEMOTHER, V3, P521

[3] TERT-BUTYL ESTERS OF AMINO ACIDS AND PEPTIDES AND THEIR USE IN PEPTIDE SYNTHESIS [J].

ANDERSON, GW ;

CALLAHAN, FM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (13) :3359-3363

[4] USE OF ESTERS OF N-HYDROXYSUCCINIMIDE IN PEPTIDE SYNTHESIS [J].

ANDERSON, GW ;

CALLAHAN, FM ;

ZIMMERMAN, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (09) :1839-+

[5] PURIFICATION AND NATURE OF THE ANTIBIOTIC NISIN [J].

BERRIDGE, NJ ;

NEWTON, GGF ;

ABRAHAM, EP .

BIOCHEMICAL JOURNAL, 1952, 52 (05) :529-535

[6]

CAMPBELL LL, 1959, FOOD TECHNOL-CHICAGO, V13, P462

[7]

CORNISHBOWDEN A, 1984, EUR J BIOCHEM, V138, P9, DOI 10.1111/j.1432-1033.1984.tb07877.x

[8] STUDIES ON SYNTHESIS OF HISTIDINE PEPTIDES .1. NIM-TOSYLHISTIDINE DERIVATIVES AS STARTING MATERIALS [J].

FUJII, T ;

SAKAKIBARA, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1974, 47 (12) :3146-3151

[9] SYNTHETIC STUDY ON PEPTIDE ANTIBIOTIC NISIN .4. SYNTHESIS OF RING D-E [J].

FUKASE, K ;

ODA, Y ;

KUBO, A ;

WAKAMIYA, T ;

SHIBA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (06) :1758-1763

[10] SYNTHETIC STUDY ON PEPTIDE ANTIBIOTIC NISIN .3. SYNTHESIS OF RING-C [J].

FUKASE, K ;

KITAZAWA, M ;

WAKAMIYA, T ;

SHIBA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (06) :1838-1840

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