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Glycobiology Advance Access published online on October 19, 2006
Glycobiology, doi:10.1093/glycob/cwl060
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© 2006 The Author(s) This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/2.0/uk/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
Received March 14, 2006
Revised September 28, 2006
Accepted October 10, 2006

Article

Biosynthesis of dTDP-6-deoxy-{beta}-D-allose, biochemical characterization of dTDP-4-keto-6-deoxyglucose reductase (GerKI) from Streptomyces sp. KCTC 0041BP

Ta Thi Thu Thuy 1, Kwangkyoung Liou 1, Tae-jin Oh 1, Dea Hee Kim 2, Doo Hyun Nam 3, Jin Cheol Yoo 4, and Jae Kyung Sohng 1 *

1 Institute of Biomolecule Reconstruction (iBR), Department of Pharmaceutical Engineering, SunMoon University, #100, Kalsan-ri, Tangjeong-myeon, Asansi, Chungnam 336-708, Korea
2 GeneChem Inc. 59-1, Jang-Dong, Yusong-Gu, Daejon, 305-390, Korea
3 Department of Pharmacy, Yeungnam University, Kyongsan, Kyungbuk, 712-749, Korea
4 Department of Pharmacy, Chosun University, Kwangju, 501-759, Korea

* To whom correspondence should be addressed.
Jae Kyung Sohng, E-mail: sohng{at}sunmoon.ac.kr


  Abstract

dTDP-6-deoxy-D-allose, an unusual deoxysugar, has been identified as an intermediate in the mycinose biosynthetic pathway of several macrolide antibiotics. In order to characterize the biosynthesis of this deoxysugar, we have cloned and heterologously overexpressed gerK1 in E. coli BL21 (DE3) cells. This gene encodes for a protein with the putative function of a dTDP-4-keto-6-deoxyglucose reductase, which appears to be involved in the dihydrochalcomycin (GERI-155) biosynthesis evidenced by Streptomyces sp KCTC 0041BP. Our results revealed that GerK1 exhibited a specific reductive effect on the 4-keto carbon of dTDP-4-keto-6-deoxy-D-allose, with the hydroxyl group in an axial configuration at the C3 position only. The enzyme catalyzed the conversion of dTDP-4-keto-6-deoxyglucose to dTDP-6-deoxy-{beta}-D-allose, according to the results of an in vitro coupled enzyme assay, in the presence of GerF (dTDP-4-keto-6-deoxyglucose 3-epimerase). The product was isolated, and its stereochemistry was determined via NMR analysis.

Keywords: Deoxysugar biosynthesis; dTDP-6-deoxy-D-allose; dTDP-4-keto-6-deoxyglucose reductase; Streptomyces.
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