The in vitro characterization of polyene glycosyltransferases AmphDI and NysDI.
The overproduction, purification, and in vitro characterization of the polyene glycosyltransferases (GTs) AmphDI and NysDI are reported. A novel nucleotidyltransferase mutant (RmlA Q83D) for the chemoenzymatic synthesis of unnatural GDP-sugar donors in conjunction with polyene GT-catalyzed sugar exchange/reverse reactions allowed the donor and acceptor specificities of these novel enzymes to be probed. The evaluation of polyene GT aglycon and GDP-sugar donor specificity revealed some tolerance to aglycon structural diversity, but stringent sugar specificity, and culminated in new polyene analogues in which L-gulose or D-mannose replace the native sugar D-mycosamine.
Zhang
Changsheng
C
Laboratory for Biosynthetic Chemistry, Pharmaceutical Sciences Division, School of Pharmacy, UW-National Cooperative Drug Discovery Group, Program, University of Wisconsin-Madison, Madison, Wisconsin 53705-2222, USA.
Moretti
Rocco
R
Jiang
Jiqing
J
Thorson
Jon S
JS
D055162:Biocatalysis; D006027:Glycosides / Q000737:chemistry / Q000378:metabolism; D016695:Glycosyltransferases / Q000235:genetics / Q000302:isolation & purification / Q000378:metabolism*; D006153:Guanosine Diphosphate / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D011090:Polyenes / Q000737:chemistry* / Q000378:metabolism*; D013302:Streptomyces / Q000201:enzymology
D006027:Glycosides; D011090:Polyenes; D006153:Guanosine Diphosphate; D016695:Glycosyltransferases
J Biol Chem. 1999 Apr 9;274(15):10133-9
10187796
Appl Microbiol Biotechnol. 2005 Aug;68(2):151-62
15821914
Trends Microbiol. 2007 May;15(5):219-32
17412593
J Am Chem Soc. 2005 Aug 3;127(30):10667-75
16045354
Chem Biol. 2000 Jun;7(6):395-403
10873841
Nat Chem Biol. 2007 Oct;3(10):657-62
17828251
Org Lett. 2006 Apr 27;8(9):1807-9
16623556
Biochim Biophys Acta. 1995 Dec 13;1240(2):167-78
8541288
J Am Chem Soc. 2007 Apr 25;129(16):5102-7
17388594
Chem Biol. 2005 Oct;12(10):1093-101
16242652
Chem Biol. 2003 Nov;10(11):1065-76
14652074
Chem Biol. 2008 Jan;15(1):78-86
18215775
J Pharm Sci. 2008 Jul;97(7):2405-25
17893903
Anal Biochem. 2008 Jun 15;377(2):251-8
18387352
Curr Med Chem. 2003 Feb;10(3):211-23
12570708
Chembiochem. 2007 Mar 5;8(4):385-90
17262863
Antimicrob Agents Chemother. 1999 Aug;43(8):1975-81
10428922
Science. 2006 Sep 1;313(5791):1291-4
16946071
J Med Chem. 2006 Apr 20;49(8):2431-9
16610786
Curr Med Chem. 2004 Jun;11(12):1645-56
15180569
Carbohydr Res. 2004 Nov 15;339(16):2641-9
15519322
Mol Microbiol. 1994 Oct;14(1):163-72
7830554
Chem Biol. 2005 May;12(5):527-34
15911373
Chem Biol. 2003 Dec;10(12):1215-24
14700629
Chem Biol. 2008 Apr;15(4):393-401
18420146
Proc Natl Acad Sci U S A. 2003 Nov 11;100(23):13184-9
14612558
Chem Biol. 2000 Nov;7(11):895-905
11094342
Chem Biol. 2001 Jul;8(7):635-44
11451665
Appl Environ Microbiol. 2007 Nov;73(22):7400-7
17905880
J Org Chem. 1998 Oct 16;63(21):7568-7572
11672420
J Am Chem Soc. 2007 Nov 14;129(45):13804-5
17956100
Proc Natl Acad Sci U S A. 2002 Oct 15;99(21):13397-402
12374866
J Biol Chem. 2007 Jun 8;282(23):16942-7
17434871
J Biol Chem. 2005 Oct 14;280(41):34420-6
16079135
J Am Chem Soc. 2005 May 4;127(17):6148-9
15853301
Biochem J. 2005 Feb 15;386(Pt 1):57-62
15228385
J Am Chem Soc. 2005 Jul 6;127(26):9336-7
15984838
Antimicrob Agents Chemother. 2004 Nov;48(11):4120-9
15504830
J Am Chem Soc. 2006 Dec 27;128(51):16420-1
17177349
Chem Biol. 2001 Jul;8(7):713-23
11451671
Appl Microbiol Biotechnol. 2003 May;61(3):179-88
12698274
Chem Biol. 2005 May;12(5):535-43
15911374
Nature. 2007 Apr 26;446(7139):1008-16
17460661
Biochim Biophys Acta. 1995 May 24;1236(1):170-6
7794947
Angew Chem Int Ed Engl. 2001 Apr 17;40(8):1502-1505
11317315
Nat Struct Biol. 2001 Jun;8(6):545-51
11373625
Chembiochem. 2003 May 9;4(5):443-6
12740816
Microbiology (Reading). 2002 Jan;148(Pt 1):51-59
11782498
Nat Biotechnol. 2003 Dec;21(12):1467-9
14608364
J Antimicrob Chemother. 2002 Feb;49 Suppl 1:1
11801573
J Am Chem Soc. 2004 Dec 29;126(51):16726-7
15612702
Angew Chem Int Ed Engl. 2008;47(23):4339-42
18442156
J Am Chem Soc. 2004 Jun 2;126(21):6534-5
15161264
Biochim Biophys Acta. 2001 Sep 3;1528(1):15-24
11514093
Curr Opin Biotechnol. 2005 Dec;16(6):622-30
16226456
J Am Chem Soc. 2005 Oct 19;127(41):14128-9
16218575
Biochem Pharmacol. 1988 Mar 1;37(5):827-36
3278711
Chem Rec. 2006;6(6):320-32
17304519
Appl Environ Microbiol. 2006 Apr;72(4):2514-9
16597951
Chem Biol. 2004 Mar;11(3):357-66
15123265
Chemistry. 2008;14(8):2465-81
18196508
Trends Genet. 1995 Jun;11(6):217-8
7638902