Enzymatic Glycosylation of Small Molecules: Challenging Substrates Require Tailored Catalysts

被引:186
作者
Desmet, Tom [2 ]
Soetaert, Wim [2 ,3 ]
Bojarova, Pavla [4 ]
Kren, Vladimir [4 ]
Dijkhuizen, Lubbert [5 ]
Eastwick-Field, Vanessa [6 ]
Schiller, Alexander [1 ]
机构
[1] Univ Jena, Inst Inorgan & Analyt Chem, D-07743 Jena, Germany
[2] Univ Ghent, Ctr Ind Biotechnol & Biocatalysis, B-9000 Ghent, Belgium
[3] BioBase Europe Pilot Plant, B-9042 Ghent, Belgium
[4] Acad Sci Czech Republ, Inst Microbiol, CR-14220 Prague, Czech Republic
[5] Univ Groningen, Groningen Biomol Sci & Biotechnol Inst GBB, NL-9700 CC Groningen, Netherlands
[6] Carbosynth Ltd, Newbury RG20 6NE, Berks, England
关键词
acceptor specificity; enzyme engineering; glycosylation; glycosyltransferase; high-throughput screening; BETA-N-ACETYLHEXOSAMINIDASE; KOENIGS-KNORR REACTIONS; RECOMBINANT SUCROSE PHOSPHORYLASE; ANOMER-SELECTIVE-GLUCOSYLATION; ACID-SUBSTITUTED VIOLOGENS; CYANIDE-PROMOTED REACTIONS; LEUCONOSTOC-MESENTEROIDES; DIRECTED EVOLUTION; CELLOBIOSE PHOSPHORYLASE; REVERSE HYDROLYSIS;
D O I
10.1002/chem.201103069
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Glycosylation can significantly improve the physicochemical and biological properties of small molecules like vitamins, antibiotics, flavors, and fragrances. The chemical synthesis of glycosides is, however, far from trivial and involves multistep routes that generate lots of waste. In this review, biocatalytic alternatives are presented that offer both stricter specificities and higher yields. The advantages and disadvantages of different enzyme classes are discussed and illustrated with a number of recent examples. Progress in the field of enzyme engineering and screening are expected to result in new applications of biocatalytic glycosylation reactions in various industrial sectors.
引用
收藏
页码:10786 / 10801
页数:16
相关论文
共 224 条
[1]   A constitutive expression system for high-throughput screening [J].
Aerts, Dirk ;
Verhaeghe, Tom ;
De Mey, Marjan ;
Desmet, Tom ;
Soetaert, Wim .
ENGINEERING IN LIFE SCIENCES, 2011, 11 (01) :10-19
[2]  
[Anonymous], 2006, ANGEW CHEM, DOI DOI 10.1002/ANGE.200504390
[3]  
[Anonymous], ANGEW CHEM
[4]   Supramolecular analytical chemistry [J].
Anslyn, Eric V. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (03) :687-699
[5]  
Auriol D., 2007, [No title captured], Patent No. [EP1867729, 1867729]
[6]  
Auriol D., 2012, PRACTICAL METHODS BI, P239
[7]  
Auriol D., 2010, [No title captured], Patent No. [EP2202237, 2202237]
[8]   Supramolecular tandem enzyme assays for multiparameter sensor arrays and enantiomeric excess determination of amino acids [J].
Bailey, David M. ;
Hennig, Andreas ;
Uzunova, Vanya D. ;
Nau, Werner M. .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (20) :6069-6077
[9]   A universal screening assay for glycosynthases: Directed evolution of glycosynthase XynB2(E335G) suggests a general path to enhance activity [J].
Ben-David, Alon ;
Shoham, Gil ;
Shoham, Yuval .
CHEMISTRY & BIOLOGY, 2008, 15 (06) :546-551
[10]   Leuconostoc mesenteroides glucansucrase synthesis of flavonoid glucosides by acceptor reactions in aqueous-organic solvents [J].
Bertrand, A ;
Morel, S ;
Lefoulon, F ;
Rolland, Y ;
Monsan, P ;
Remaud-Simeon, M .
CARBOHYDRATE RESEARCH, 2006, 341 (07) :855-863