BIOSYNTHESIS OF LACTACYSTIN

被引：19

作者：

TAKAHASHI, S

UCHIDA, K

NAKAGAWA, A

机构：

[1] TEIKYO UNIV,DEPT BIOSCI,UTSUNOMIYA,TOCHIGI 320,JAPAN

[2] TOKYO METROPOLITAN UNIV,FAC SCI,HACHIOJI,TOKYO 192,JAPAN

[3] KITASATO UNIV,SCH PHARMACEUT SCI,MINATO KU,TOKYO 108,JAPAN

[4] KITASATO INST,MINATO KU,TOKYO 108,JAPAN

来源：

JOURNAL OF ANTIBIOTICS | 1995年 / 48卷 / 09期

关键词：

D O I：

10.7164/antibiotics.48.1015

中图分类号：

Q81 [生物工程学（生物技术）]; Q93 [微生物学];

学科分类号：

071005 ; 0836 ; 090102 ; 100705 ;

摘要：

The biosynthesis of lactacystin, a new microbial metabolite which induces differentiation of neuroblastoma cells, was studied by the feeding experiments of various C-13-labeled compounds and NMR spectroscopic analysis. The feeding experiments showed that lactacystin consists of three biosynthetic units, namely isobutyrate (and/or L-valine), L-leucine and L-cysteine. The C-10 unit containing gamma-lactam moiety arises by a condensation between methylmalonic semialdehyde and C-alpha position of L-leucine, followed by intramolecular cyclization. Two diastereotopic methyls, C-11 and C-12 of lactacystin were found to originate from the pro-R and pro-S methyls of leucine, respectively, as shown by incorporating a new type of chiral C-13-labeled L-leucine.

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页码：1015 / 1020

页数：6

相关论文

共 14 条

[1] USE OF CHIRAL ISOPROPYL GROUPS IN BIOSYNTHESIS - SYNTHESIS OF (2RS,3S)-[4-C-13]VALINE [J].

BALDWIN, JE ;

LOLIGER, J ;

RASTETTER, W ;

NEUSS, N ;

HUCKSTEP, LL ;

DELAHIGU.N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (11) :3796-3797

[2]

KAINOSHO M, 1990, Patent No. 291284

[3] SYNTHESIS AND INCORPORATION OF (2S,3S)-[4-C-13]VALINE INTO BETA-LACTAM ANTIBIOTICS [J].

KLUENDER, H ;

BRADLEY, CH ;

SIH, CJ ;

FAWCETT, P ;

ABRAHAM, EP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (18) :6149-6150

[4] STRUCTURE OF OXAZOLOMYCIN, A NOVEL BETA-LACTONE ANTIBIOTIC [J].

MORI, T ;

TAKAHASHI, K ;

KASHIWABARA, M ;

UEMURA, D ;

KATAYAMA, C ;

IWADARE, S ;

SHIZURI, Y ;

MITOMO, R ;

NAKANO, F ;

MATSUZAKI, A .

TETRAHEDRON LETTERS, 1985, 26 (08) :1073-1076

[5] BIOSYNTHESIS OF ASUKAMYCIN - FORMATION OF THE 2-AMINO-3-HYDROXYCYCLOPENT-2-ENONE MOIETY [J].

NAKAGAWA, A ;

WU, TS ;

KELLER, PJ ;

LEE, JP ;

OMURA, S ;

FLOSS, HG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (08) :519-521

[6] BIOSYNTHESIS OF LACTACYSTIN - ORIGIN OF THE CARBONS AND STEREOSPECIFIC NMR ASSIGNMENT OF THE 2 DIASTEREOTOPIC METHYL-GROUPS [J].

NAKAGAWA, A ;

TAKAHASHI, S ;

UCHIDA, K ;

MATSUZAKI, K ;

OMURA, S ;

NAKAMURA, A ;

KURIHARA, N ;

NAKAMATSU, T ;

MIYAKE, Y ;

TAKE, K ;

KAINOSHO, M .

TETRAHEDRON LETTERS, 1994, 35 (28) :5009-5012

[7] STEREOSPECIFIC NUCLEAR MAGNETIC-RESONANCE ASSIGNMENTS OF THE METHYL-GROUPS OF VALINE AND LEUCINE IN THE DNA-BINDING DOMAIN OF THE 434-REPRESSOR BY BIOSYNTHETICALLY DIRECTED FRACTIONAL C-13 LABELING [J].

NERI, D ;

SZYPERSKI, T ;

OTTING, G ;

SENN, H ;

WUTHRICH, K .

BIOCHEMISTRY, 1989, 28 (19) :7510-7516

[8] INCORPORATION OF (2RS,3S)-[4-C-13]VALINE INTO CEPHALOSPORIN-C [J].

NEUSS, N ;

NASH, CH ;

BALDWIN, JE ;

LEMKE, PA ;

GRUTZNER, JB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (11) :3797-3798

[9]

NOLLER CR, 1943, ORG SYN COLL, V7, P358

[10] A MILD AND EFFICIENT ROUTE TO SCHIFF-BASE DERIVATIVES OF AMINO-ACIDS [J].

ODONNELL, MJ ;

POLT, RL .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (13) :2663-2666