Enzymatic methods for glyco(diversification/randomization) of drugs and small molecules

被引：221

作者：

Gantt, Richard W. ^{[1
]}

Peltier-Pain, Pauline ^{[1
]}

Thorson, Jon S. ^{[1
]}

机构：

[1] Univ Wisconsin, Wisconsin Ctr Nat Prod Res, Sch Pharm, Div Pharmaceut Sci, Madison, WI 53705 USA

来源：

NATURAL PRODUCT REPORTS | 2011年 / 28卷 / 11期

关键词：

BIOSYNTHETIC GENE-CLUSTER; UDP-SUGAR PYROPHOSPHORYLASE; IN-VITRO CHARACTERIZATION; NATURAL-PRODUCT GLYCOSYLTRANSFERASE; RECOMBINANT SUCROSE PHOSPHORYLASE; ESCHERICHIA-COLI GALACTOKINASE; GDP-MANNOSE PYROPHOSPHORYLASE; BROAD SUBSTRATE-SPECIFICITY; POLYENE MACROLIDE PIMARICIN; LARGE-SCALE SYNTHESIS;

D O I：

10.1039/c1np00045d

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Glyco(randomization/diversification) is a term that encompasses strategies to diversify a core drug scaffold via enzymatic glycosylation to provide sets of analogs wherein the sole diversity element is a carbohydrate. This review covers the influence of glycosylation upon various drug properties, the classes of glycosyl-conjugating enzymes amenable to glyco(randomization/diversification) schemes, approaches to the synthesis of required substrates and specific examples of glycorandomized libraries utilizing both wild-type and engineered enzymes.

引用

页码：1811 / 1853

页数：43

共 375 条

[1] Chemical Approaches To Perturb, Profile, and Perceive Glycans [J].

Agard, Nicholas J. ;

Bertozzi, Carolyn R. .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (06) :788-797

[2] High-throughput screening methodology for the directed evolution of glycosyltransferases [J].

Aharoni, Amir ;

Thieme, Karena ;

Chiu, Cecilia P. C. ;

Buchini, Sabrina ;

Lairson, Luke L. ;

Chen, Hongming ;

Strynadka, Natalie C. J. ;

Wakarchuk, Warren W. ;

Withers, Stephen G. .

NATURE METHODS, 2006, 3 (08) :609-614

[3] The calicheamicin gene cluster and its iterative type I enediyne PKS [J].

Ahlert, J ;

Shepard, E ;

Lomovskaya, N ;

Zazopoulos, E ;

Staffa, A ;

Bachmann, BO ;

Huang, KX ;

Fonstein, L ;

Czisny, A ;

Whitwam, RE ;

Farnet, CM ;

Thorson, JS .

SCIENCE, 2002, 297 (5584) :1173-1176

[4] Colchicine glycorandomization influences cytotoxicity and mechanism of action [J].

Ahmed, Aqeel ;

Peters, Noel R. ;

Fitzgeraldo, Megan K. ;

Watson, James A., Jr. ;

Hoffmann, F. Michael ;

Thorson, Jon S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (44) :14224-14225

[5] Hypoxic regulation of glucose transport, anaerobic metabolism and angiogenesis in cancer: Novel pathways and targets for anticancer therapeutics [J].

Airley, Rachel E. ;

Mobasheri, Ali .

CHEMOTHERAPY, 2007, 53 (04) :233-256

[6] Substrate specificity of NovM: Implications for novobiocin biosynthesis and glycorandomization [J].

Albermann, C ;

Soriano, A ;

Jiang, JQ ;

Vollmer, H ;

Biggins, JB ;

Barton, WA ;

Lesniak, J ;

Nikolov, DB ;

Thorson, JS .

ORGANIC LETTERS, 2003, 5 (06) :933-936

[7] Anticancer drugs from nature - natural products as a unique source of new microtubule-stabilizing agents [J].

Altmann, Karl-Heinz ;

Gertsch, Juerg .

NATURAL PRODUCT REPORTS, 2007, 24 (02) :327-357

[8] Anti-inflammatory effects of macrolides - an underappreciated benefit in the treatment of community-acquired respiratory tract infections and chronic inflammatory pulmonary conditions? [J].

Amsden, GW .

JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 2005, 55 (01) :10-21

[9] Sucrose-Utilizing Transglucosidases for Biocatalysis [J].

Andre, Isabelle ;

Potocki-Veronese, Gabrielle ;

Morel, Sandrine ;

Monsan, Pierre ;

Remaud-Simeon, Magali .

CARBOHYDRATES IN SUSTAINABLE DEVELOPMENT I: RENEWABLE RESOURCES FOR CHEMISTRY AND BIOTECHNOLOGY, 2010, 294 :25-48

[10] Large-scale in vivo synthesis of the carbohydrate moieties of gangliosides GM1 and GM2 by metabolically engineered Escherichia coli [J].

Antoine, T ;

Priem, B ;

Heyraud, A ;

Greffe, L ;

Gilbert, M ;

Wakarchuk, BW ;

Lam, JS ;

Samain, E .

CHEMBIOCHEM, 2003, 4 (05) :406-412

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