Literature DB >> 22018788

Enzymatic synthesis of D-sorbose and D-psicose with aldolase RhaD: effect of acceptor configuration on enzyme stereoselectivity.

Zijie Li1, Li Cai, Qingsheng Qi, Peng George Wang.   

Abstract

It was previously reported that DHAP-dependent aldolase RhaD selectively chooses L-glyceraldehyde from racemic glyceraldehyde to produce l-fructose exclusively. Contrastingly, we discovered that D-glyceraldehyde is also tolerated as an acceptor and the stereoselectivity of the enzyme is lost in the corresponding aldol addition. Furthermore, we applied this property to efficiently synthesize two rare sugars D-sorbose and D-psicose. Copyright Â
© 2011 Elsevier Ltd. All rights reserved.

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Year:  2011        PMID: 22018788      PMCID: PMC3210396          DOI: 10.1016/j.bmcl.2011.09.087

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  17 in total

Review 1.  Recent progress in stereoselective synthesis with aldolases.

Authors:  Pere Clapés; Wolf-Dieter Fessner; Georg A Sprenger; Anne K Samland
Journal:  Curr Opin Chem Biol       Date:  2010-01-12       Impact factor: 8.822

Review 2.  Enzyme mediated C-C bond formation.

Authors:  W D Fessner
Journal:  Curr Opin Chem Biol       Date:  1998-02       Impact factor: 8.822

3.  Production of D- and L-xylulose by mutants of Klebsiella pneumoniae and Erwinia uredovora.

Authors:  R C Doten; R P Mortlock
Journal:  Appl Environ Microbiol       Date:  1985-01       Impact factor: 4.792

Review 4.  Chemical and enzymatic routes to dihydroxyacetone phosphate.

Authors:  Michael Schümperli; René Pellaux; Sven Panke
Journal:  Appl Microbiol Biotechnol       Date:  2007-02-22       Impact factor: 4.813

5.  Fructose-6-phosphate aldolase in organic synthesis: preparation of D-fagomine, N-alkylated derivatives, and preliminary biological assays.

Authors:  José A Castillo; Jordi Calveras; Josefina Casas; Montserrat Mitjans; M Pilar Vinardell; Teodor Parella; Tomoyuki Inoue; Georg A Sprenger; Jesús Joglar; Pere Clapés
Journal:  Org Lett       Date:  2006-12-21       Impact factor: 6.005

6.  Efficient production of L-ribose with a recombinant Escherichia coli biocatalyst.

Authors:  Ryan D Woodyer; Nathan J Wymer; F Michael Racine; Shama N Khan; Badal C Saha
Journal:  Appl Environ Microbiol       Date:  2008-03-14       Impact factor: 4.792

Review 7.  Carbon-carbon coupling in biotransformation.

Authors:  Michael Breuer; Bernhard Hauer
Journal:  Curr Opin Biotechnol       Date:  2003-12       Impact factor: 9.740

8.  One-pot synthesis of L-Fructose using coupled multienzyme systems based on rhamnulose-1-phosphate aldolase.

Authors:  Dirk Franke; Timothy Machajewski; Che-Chang Hsu; Chi-Huey Wong
Journal:  J Org Chem       Date:  2003-08-22       Impact factor: 4.354

9.  A new strategy for the cloning, overexpression and one step purification of three DHAP-dependent aldolases: rhamnulose-1-phosphate aldolase, fuculose-1-phosphate aldolase and tagatose-1,6-diphosphate aldolase.

Authors:  E Garcia-Junceda; G J Shen; T Sugai; C H Wong
Journal:  Bioorg Med Chem       Date:  1995-07       Impact factor: 3.641

10.  Conversion shift of D-fructose to D-psicose for enzyme-catalyzed epimerization by addition of borate.

Authors:  Nam-Hee Kim; Hye-Jung Kim; Dong-Il Kang; Ki-Woong Jeong; Jung-Kul Lee; Yangmee Kim; Deok-Kun Oh
Journal:  Appl Environ Microbiol       Date:  2008-03-31       Impact factor: 4.792

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  7 in total

1.  One-pot four-enzyme synthesis of ketoses with fructose 1,6-bisphosphate aldolases from Staphylococcus carnosus and rabbit muscle.

Authors:  Zijie Li; Li Cai; Mohui Wei; Peng George Wang
Journal:  Carbohydr Res       Date:  2012-05-15       Impact factor: 2.104

2.  Facile Enzymatic Synthesis of Ketoses.

Authors:  Liuqing Wen; Kenneth Huang; Mohui Wei; Jeffrey Meisner; Yunpeng Liu; Kristina Garner; Lanlan Zang; Xuan Wang; Xu Li; Junqiang Fang; Houcheng Zhang; Peng George Wang
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-14       Impact factor: 15.336

3.  Biosynthesis of l-Sorbose and l-Psicose Based on C-C Bond Formation Catalyzed by Aldolases in an Engineered Corynebacterium glutamicum Strain.

Authors:  Jiangang Yang; Jitao Li; Yan Men; Yueming Zhu; Ying Zhang; Yuanxia Sun; Yanhe Ma
Journal:  Appl Environ Microbiol       Date:  2015-04-17       Impact factor: 4.792

4.  Efficient enzymatic synthesis of L-rhamnulose and L-fuculose.

Authors:  Liuqing Wen; Lanlan Zang; Kenneth Huang; Shanshan Li; Runling Wang; Peng George Wang
Journal:  Bioorg Med Chem Lett       Date:  2015-12-17       Impact factor: 2.823

5.  Construction of microbial platform for an energy-requiring bioprocess: practical 2'-deoxyribonucleoside production involving a C-C coupling reaction with high energy substrates.

Authors:  Nobuyuki Horinouchi; Takafumi Sakai; Takako Kawano; Seiichiro Matsumoto; Mie Sasaki; Makoto Hibi; Jun Shima; Sakayu Shimizu; Jun Ogawa
Journal:  Microb Cell Fact       Date:  2012-06-15       Impact factor: 5.328

Review 6.  Biosynthesis of rare hexoses using microorganisms and related enzymes.

Authors:  Zijie Li; Yahui Gao; Hideki Nakanishi; Xiaodong Gao; Li Cai
Journal:  Beilstein J Org Chem       Date:  2013-11-12       Impact factor: 2.883

7.  Structure-based prediction and identification of 4-epimerization activity of phosphate sugars in class II aldolases.

Authors:  Seon-Hwa Lee; Seung-Hye Hong; Jung-Ung An; Kyoung-Rok Kim; Dong-Eun Kim; Lin-Woo Kang; Deok-Kun Oh
Journal:  Sci Rep       Date:  2017-05-16       Impact factor: 4.379

  7 in total

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