NALPHA-ACETYLFUSARININES - ISOLATION, CHARACTERIZATION, AND PROPERTIES

被引:46
作者
MOORE, RE [1 ]
EMERY, T [1 ]
机构
[1] UTAH STATE UNIV, DEPT CHEM & BIOCHEM, LOGAN, UT 84322 USA
关键词
D O I
10.1021/bi00658a001
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The isolation, purification and structural elucidation of a new group of naturally occurring hydroxamic acids are described. These compounds are produced by an unidentified species of Penicillium when grown on Fe deficient medium. They are closely related structurally to the fusarinines, whose basic structure contains N.delta.-(cis-5-hydroxy-3-methylpent-2-enoyl)-N.delta.-hydroxy-L-ornithine, but the .alpha.-amino groups in the new compounds are protected by N.alpha.-acetyl groups. The most complex of the compounds is N,N'',N"-triacetylfusarinine C, or N,N'',N"-triacetylfusigen, a cyclic triester composed of 3 molecules of N.alpha.-acetylfusarinine. The trimer has growth factor activity for Arthrobacter JG-9 about equal to fusarinine C itself. The monohydroxamate, N.alpha.-acetylfusarinine, is more active than the trimer. The greater chemical stability of these compounds compared to the unacetylated fusarinines reconciles the utilization of otherwise unstable amino acid esters as Fe transport agents.
引用
收藏
页码:2719 / 2723
页数:5
相关论文
共 16 条
[1]   RHODOTORULIC ACID A DIKETOPIPERAZINE DIHYDROXAMIC ACID WITH GROWTH-FACTOR ACTIVITY .I. ISOLATION AND CHARACTERIZATION [J].
ATKIN, CL ;
NEILANDS, JB .
BIOCHEMISTRY, 1968, 7 (10) :3734-&
[2]  
CHINARD FP, 1952, J BIOL CHEM, V199, P91
[3]   CONSTITUTION OF FUSIGEN AND ITS DEGRADATION TO DELTA2-ANHYDROMEVALONIC ACID LACTONE [J].
DIEKMANN, H ;
ZAHNER, H .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1967, 3 (02) :213-&
[4]   METABOLIC PRODUCTS OF MICROORGANISMS .150. FERRICROCIN, TRIACETYLFUSIGEN AND OTHER SIDERAMINES FROM FUNGI OF GENUS ASPERGILLUS, GROUP FUMIGATUS [J].
DIEKMANN, H ;
KREZDORN, E .
ARCHIVES OF MICROBIOLOGY, 1975, 106 (03) :191-194
[5]  
EMERY T, 1971, ADV ENZYMOL RAMB, V35, P135
[7]   FUNGAL ORNITHINE ESTERASES - RELATIONSHIP TO IRON TRANSPORT [J].
EMERY, T .
BIOCHEMISTRY, 1976, 15 (13) :2723-2728
[8]   BIOLOGICAL-ACTIVITY OF SOME SIDEROCHROME DERIVATIVES [J].
EMERY, T ;
EMERY, L .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1973, 50 (03) :670-675
[10]   ACYLATION OF NDELTA-BENZYLOXYORNITHINE [J].
ISOWA, Y ;
KURITA, H ;
TAKASHIM.T ;
SATO, M ;
MORI, K ;
OHMORI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1972, 45 (05) :1464-+