Abyssomicin C -: A polycyclic antibiotic from a marine Verrucosispora strain as an inhibitor of the p-aminobenzoic acid/tetrahydrofolate biosynthesis pathway

被引:247
作者
Bister, B
Bischoff, D
Ströbele, M
Riedlinger, J
Reicke, A
Wolter, F
Bull, AT
Zähner, H
Fiedler, HP
Süssmuth, RD
机构
[1] Univ Tubingen, Inst Organ Chem, D-72076 Tubingen, Germany
[2] Univ Tubingen, Inst Anorgan Chem, D-72076 Tubingen, Germany
[3] Univ Tubingen, Inst Mikrobiol, D-72076 Tubingen, Germany
[4] Univ Kent, Res Sch Biosci, Canterbury CT2 7NJ, Kent, England
关键词
antibiotics; metabolism; Michael addition; natural products;
D O I
10.1002/anie.200353160
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Plumbing the depths: Abyssomicin C (structure shown) from ocean floor sediment is a novel antibiotic that inhibits the biosynthesis steps between chorismate and p-aminobenzoic acid. Its activity may be explained by the irreversible trapping of the targeted enzymes by a Michael addition. Blocking the biosynthesis of p-aminobenzoic acid may be one approach to developing new antibiotics.
引用
收藏
页码:2574 / 2576
页数:3
相关论文
共 16 条
[1]  
*AM CHEM SOC, SCIF SCHOL VERS 2002
[2]  
[Anonymous], 1993, NAT PROD LETT
[3]   CHORISMATE MUTASE INHIBITORS - SYNTHESIS AND EVALUATION OF SOME POTENTIAL TRANSITION-STATE ANALOGS [J].
BARTLETT, PA ;
NAKAGAWA, Y ;
JOHNSON, CR ;
REICH, SH ;
LUIS, A .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) :3195-3210
[4]   The folic acid biosynthesis pathway in bacteria: evaluation of potential for antibacterial drug discovery [J].
Bermingham, A ;
Derrick, JP .
BIOESSAYS, 2002, 24 (07) :637-648
[5]  
Braun S., 1998, 150 MORE BASIC NMR E, P266
[6]  
COPLEY SD, 1987, J AM CHEM SOC, V109, P5009
[7]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[8]  
HELMCHEN G, 1974, TETRAHEDRON LETT, P1527
[9]  
HELMCHEN G, 1995, METHODEN ORG CHE E A, V21, P253
[10]   THE STRUCTURE OF TETRONOLIDE, THE AGLYCONE OF ANTI-TUMOR ANTIBIOTIC TETROCARCIN [J].
HIRAYAMA, N ;
KASAI, M ;
SHIRAHATA, K ;
OHASHI, Y ;
SASADA, Y .
TETRAHEDRON LETTERS, 1980, 21 (26) :2559-2560