Biocatalytic Synthesis of Pikromycin, Methymycin, Neomethymycin, Novamethymycin, and Ketomethymycin

被引：48

作者：

Hansen, Douglas A. ^{[1
,2
]}

Rath, Christopher M. ^{[2
]}

Eisman, Eli B. ^{[2
]}

Narayan, Alison R. H. ^{[2
]}

Kittendorf, Jeffrey D. ^{[2
,5
]}

Mortison, Jonathan D. ^{[2
,3
]}

Yoon, Yeo Joon ^{[6
]}

Sherman, David H. ^{[1
,2
,3
,4
]}

机构：

[1] Univ Michigan, Dept Med Chem, Ann Arbor, MI 48109 USA

[2] Univ Michigan, Inst Life Sci, Ann Arbor, MI 48109 USA

[3] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

[4] Univ Michigan, Dept Microbiol & Immunol, Ann Arbor, MI 48109 USA

[5] Alluvium Biosci, Ann Arbor, MI 48108 USA

[6] Ewha Womans Univ, Div Nano Sci, Seoul 120750, South Korea

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 30期

关键词：

DESMETHYL MACROLIDES SYNTHESIS; ASYMMETRIC TOTAL-SYNTHESIS; PRACTICAL CHIRAL AUXILIARY; 6-DEOXYERYTHRONOLIDE B; POLYKETIDE SYNTHASE; ERYTHROMYCIN; EFFICIENT; OXIDATION; ACID; MACROLACTONIZATION;

D O I：

10.1021/ja404134f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A biocatalytic platform that employs the final two monomodular type I polyketide synthases of the pikromycin pathway in vitro followed by direct appendage of D-desosamine and final C-H oxidation(s) in vivo was developed and applied toward the synthesis of a suite of 12- and 14-membered ring macrolide natural products. This methodology delivered both compound classes in 13 steps (longest linear sequence) from commercially available (R)-Roche ester in >10% overall yields.

引用

页码：11232 / 11238

页数：7

共 57 条

[1] Structural basis for macrolactonization by the pikromycin thioesterase
Akey, David L.
Kittendorf, Jeffrey D.
Giraldes, John W.
Fecik, Robert A.
Sherman, David H.
Smith, Janet L.
[J]. NATURE CHEMICAL BIOLOGY, 2006, 2 (10) : 537 - 542
[2] Chemoenzymatic synthesis of the polyketide macrolactone 10-deoxymethynolide
Aldrich, CC
Venkatraman, L
Sherman, DH
Fecik, RA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) : 8910 - 8911
[3] Biochemical investigation of pikromycin biosynthesis employing native penta- and hexaketide chain elongation intermediates
Aldrich, CC
Beck, BJ
Fecik, RA
Sherman, DH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (23) : 8441 - 8452
[4] Engineering the third wave of biocatalysis
Bornscheuer, U. T.
Huisman, G. W.
Kazlauskas, R. J.
Lutz, S.
Moore, J. C.
Robins, K.
[J]. NATURE, 2012, 485 (7397) : 185 - 194
[5] PIKROMYCIN, EIN NEUES ANTIBIOTIKUM AUS ACTINOMYCETEN
BROCKMANN, H
HENKEL, W
[J]. NATURWISSENSCHAFTEN, 1950, 37 (06) : 138 - 139
[6] ANTIBIOTICA AUS ACTINOMYCCTEN .6. PIKROMYCIN, EIN BITTER SCHMECKENDES ANTIBIOTICUM AUS ACTINOMYCETEN
BROCKMANN, H
HENKEL, W
[J]. CHEMISCHE BERICHTE-RECUEIL, 1951, 84 (03): : 284 - 288
[7] IDENTIFICATION OF DEBS-1, DEBS-2 AND DEBS-3, THE MULTIENZYME POLYPEPTIDES OF THE ERYTHROMYCIN-PRODUCING POLYKETIDE SYNTHASE FROM SACCHAROPOLYSPORA-ERYTHRAEA
CAFFREY, P
BEVITT, DJ
STAUNTON, J
LEADLAY, PF
[J]. FEBS LETTERS, 1992, 304 (2-3) : 225 - 228
[8] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS
CARLSEN, PHJ
KATSUKI, T
MARTIN, VS
SHARPLESS, KB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) : 3936 - 3938
[9] A general model for selectivity in olefin cross metathesis
Chatterjee, AK
Choi, TL
Sanders, DP
Grubbs, RH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) : 11360 - 11370
[10] Expression, purification, and characterization of two N,N-dimethyltransferases, TylM1 and DesVI, involved in the biosynthesis of mycaminose and desosamine
Chen, HW
Yamase, H
Murakami, K
Chang, CW
Zhao, LS
Zhao, ZB
Liu, HW
[J]. BIOCHEMISTRY, 2002, 41 (29) : 9165 - 9183

← 1 2 3 4 5 6 →