Synthesis of long-chain fatty acid enol esters isolated from an environmental DNA clone

被引：20

作者：

Brady, SF ^{[1
]}

Clardy, J ^{[1
]}

机构：

[1] Cornell Univ, Baker Lab, Dept Chem & Chem Biol, Ithaca, NY 14853 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 02期

关键词：

D O I：

10.1021/ol0267681

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Long-chain fatty acid enol ester 1 is the major metabolite of a new family of small molecules isolated from the heterologous expression of environmentally derived DNA. A versatile synthesis of 1, in which an aromatic acetaldehyde is O-acylated with a long-chain acyl chloride allowed for the-rapid construction of both the isolated product (1) and a-number of structural analogues (including 8, 17, and 18).

引用

页码：121 / 124

页数：4

共 16 条

[1] New natural product families from an environmental DNA (eDNA) gene cluster [J].

Brady, SF ;

Chao, CJ ;

Clardy, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (34) :9968-9969

[2] Cloning and heterologous expression of a natural product biosynthetic gene cluster from eDNA [J].

Brady, SF ;

Chao, CJ ;

Handelsman, J ;

Clardy, J .

ORGANIC LETTERS, 2001, 3 (13) :1981-1984

[3] Long-chain N-acyl amino acid antibiotics isolated from heterologously expressed environmental DNA [J].

Brady, SF ;

Clardy, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) :12903-12904

[4] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].

COREY, EJ ;

VENKATESWARLU, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+

[5] Isolation of antibiotics turbomycin A and B from a metagenomic library of soil microbial DNA [J].

Gillespie, DE ;

Brady, SF ;

Bettermann, AD ;

Cianciotto, NP ;

Liles, MR ;

Rondon, MR ;

Clardy, J ;

Goodman, RM ;

Handelsman, J .

APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 2002, 68 (09) :4301-4306

[6] Impact of culture-independent studies on the emerging phylogenetic view of bacterial diversity [J].

Hugenholtz, P ;

Goebel, BM ;

Pace, NR .

JOURNAL OF BACTERIOLOGY, 1998, 180 (18) :4765-4774

[7]

LADJAMA D, 1979, SYNTHESIS-STUTTGART, P504

[8] Selective deprotection of alkyl vs. aryl silyl ethers [J].

Lipshutz, BH ;

Keith, J .

TETRAHEDRON LETTERS, 1998, 39 (17) :2495-2498

[9] OXIDATION OF LONG-CHAIN AND RELATED ALCOHOLS TO CARBONYLS BY DIMETHYL-SULFOXIDE ACTIVATED BY OXALYL CHLORIDE [J].

MANCUSO, AJ ;

HUANG, SL ;

SWERN, D .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) :2480-2482

[10] Enzymatic synthesis of a quorum-sensing autoinducer through use of defined substrates [J].

More, MI ;

Finger, LD ;

Stryker, JL ;

Fuqua, C ;

Eberhard, A ;

Winans, SC .

SCIENCE, 1996, 272 (5268) :1655-1658

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