Biosynthesis of volatiles by the myxobacterium Myxococcus xanthus

被引:104
作者
Dickschat, JS
Wenzel, SC
Bode, HB
Müller, R
Schulz, S
机构
[1] Gesell Biotechnol Forsch mbH, D-38124 Braunschweig, Germany
[2] Tech Univ Braunschweig, Inst Organ Chem, D-38106 Braunschweig, Germany
关键词
biosynthesis; mass spectrometry; myxobacteria; polyketides; volatile compounds;
D O I
10.1002/cbic.200300813
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 volatiles emitted from cell cultures of myxobacterium Myxococcus xanthus were collected by use of a closed-loop stripping apparatus (CLSA) and analyzed by GC-MS. Two new natural products, (S)-9-methyldecan-3-ol ((S)-1) and 9-methyldecan-3-one (2), were identified and synthesized, together with other aliphatic ketones and alcohols, and terpenes, Biosynthesis, of the two main components (S)-1 2 was examined in feeding experiments carried out with the wild-type strain DK1622 and two mutant strains JD300 and KD11017, which are impaired in the degradation pathway from leucine to isovaleryl-SCoA. Isovaleryl-SCoA is used as a starter, followed by chain elongation with two malonate units. Subsequent use of methyl malonate and decarboxylation leads to (S)-1 and 2. Furthermore, 3,3-dimethylacrylic acid (DMAA) can be used by the mutant strain to form isovaleryl- SCoA, which corroborates, recent data on the detection of a novel variety of the mevalonate pathway giving rise to isovaleryl-SCoA from HMGCoA.
引用
收藏
页码:778 / 787
页数:10
相关论文
共 35 条
[1]  
[Anonymous], 1984, ANAL VOLATILES
[2]   Metabolic diversity in myxobacteria:: identification of the myxalamid and the stigmatellin biosynthetic gene cluster of Stigmatella aurantiaca Sg a15 and a combined polyketide-(poly)peptide gene cluster from the epothilone producing strain Sorangium cellulosum So ce90 [J].
Beyer, S ;
Kunze, B ;
Silakowski, B ;
Müller, R .
BIOCHIMICA ET BIOPHYSICA ACTA-GENE STRUCTURE AND EXPRESSION, 1999, 1445 (02) :185-195
[3]  
BODE H, UNPUB
[4]  
Bohlendorf B, 1996, LIEBIGS ANN, P49
[5]   Epothilones: new tubulin polymerization agents in preclinical and clinical development [J].
Borzilleri, RM ;
Vite, GD .
DRUGS OF THE FUTURE, 2002, 27 (12) :1149-1163
[6]   BRANCHED-CHAIN FATTY-ACIDS - THE CASE FOR A NOVEL FORM OF CELL-CELL SIGNALING DURING MYXOCOCCUS-XANTHUS DEVELOPMENT [J].
DOWNARD, J ;
TOAL, D .
MOLECULAR MICROBIOLOGY, 1995, 16 (02) :171-175
[7]   The biosynthesis of the aromatic myxobacterial electron transport inhibitor stigmatellin is directed by a novel type of modular polyketide synthase [J].
Gaitatzis, N ;
Silakowski, B ;
Kunze, B ;
Nordsiek, G ;
Blöcker, H ;
Höfle, G ;
Müller, R .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2002, 277 (15) :13082-13090
[8]   Epothilons A and B: Antifungal and cytotoxic compounds from Sorangium cellulosum (Myxobacteria) - Production, physico-chemical and biological properties [J].
Gerth, K ;
Bedorf, N ;
Hofle, G ;
Irschik, H ;
Reichenbach, H .
JOURNAL OF ANTIBIOTICS, 1996, 49 (06) :560-563
[9]   Myxobacteria:: proficient producers of novel natural products with various biological activities -: past and future biotechnological aspects with the focus on the genus Sorangium [J].
Gerth, K ;
Pradella, S ;
Perlova, O ;
Beyer, S ;
Müller, R .
JOURNAL OF BIOTECHNOLOGY, 2003, 106 (2-3) :233-253
[10]   ME3SICL/HMPA ACCELERATED CONJUGATE ADDITION OF CATALYTIC COPPER REAGENT - STEREOSELECTIVE SYNTHESIS OF ENOL SILYL ETHER OF ALDEHYDE [J].
HORIGUCHI, Y ;
MATSUZAWA, S ;
NAKAMURA, E ;
KUWAJIMA, I .
TETRAHEDRON LETTERS, 1986, 27 (34) :4025-4028