General Tolerance of Galactosyltransferases toward UDP-galactosamine Expands Their Synthetic Capability.


Journal

Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543

Informations de publication

Date de publication:
13 12 2021
Historique:
received: 15 09 2021
pubmed: 19 10 2021
medline: 28 12 2021
entrez: 18 10 2021
Statut: ppublish

Résumé

Accessing large numbers of structurally diverse glycans and derivatives is essential to functional glycomics. We showed a general tolerance of galactosyltransferases toward uridine-diphosphate-galactosamine (UDP-GalN), which is not a commonly used sugar nucleotide donor. The property was harnessed to develop a two-step chemoenzymatic strategy for facile synthesis of novel and divergent N-acetylgalactosamine (GalNAc)-glycosides and derivatives in preparative scales. The discovery and the application of the new property of existing glycosyltransferases expand their catalytic capabilities in generating novel carbohydrate linkages, thus prompting the synthesis of diverse glycans and glycoconjugates for biological studies.

Identifiants

pubmed: 34661966
doi: 10.1002/anie.202112574
pmc: PMC8720041
mid: NIHMS1751750
doi:

Substances chimiques

uridine diphosphate galactosamine 17479-06-0
Uridine Diphosphate N-Acetylgalactosamine 7277-98-7
Galactosyltransferases EC 2.4.1.-

Types de publication

Journal Article Research Support, N.I.H., Extramural

Langues

eng

Sous-ensembles de citation

IM

Pagination

26555-26560

Subventions

Organisme : NIGMS NIH HHS
ID : R44 GM123820
Pays : United States
Organisme : NIGMS NIH HHS
ID : U01GM125288
Pays : United States
Organisme : NIGMS NIH HHS
ID : U01 GM125288
Pays : United States
Organisme : NIGMS NIH HHS
ID : R44GM123820
Pays : United States
Organisme : NIA NIH HHS
ID : R56AG062258
Pays : United States
Organisme : NIA NIH HHS
ID : R56 AG062258
Pays : United States

Informations de copyright

© 2021 Wiley-VCH GmbH.

Références

EMBO J. 2001 Feb 15;20(4):638-49
pubmed: 11179209
Angew Chem Int Ed Engl. 2006 Jun 12;45(24):3938-44
pubmed: 16721893
Annu Rev Biochem. 2016 Jun 2;85:599-630
pubmed: 27145845
Bioorg Med Chem Lett. 2009 Sep 15;19(18):5433-5
pubmed: 19683921
Org Biomol Chem. 2020 Apr 29;18(16):3142-3148
pubmed: 32255449
J Am Chem Soc. 2013 Oct 2;135(39):14831-9
pubmed: 24044869
Proc Natl Acad Sci U S A. 2017 Jul 3;114(27):6954-6959
pubmed: 28630345
Org Biomol Chem. 2018 Jun 6;16(22):4076-4080
pubmed: 29789847
Anal Biochem. 1983 Jul 15;132(2):405-12
pubmed: 6625174
Exp Oncol. 2007 Mar;29(1):61-6
pubmed: 17431391
Nat Commun. 2021 Jun 11;12(1):3573
pubmed: 34117223
Carbohydr Res. 2012 Jul 1;355:35-9
pubmed: 22633137
J Org Chem. 2016 Jul 15;81(14):5851-65
pubmed: 27305319
Angew Chem Int Ed Engl. 2018 Jul 16;57(29):9003-9007
pubmed: 29802667
J Biol Chem. 2002 Jun 7;277(23):20833-9
pubmed: 11916963
ACS Catal. 2019 Dec 6;9(12):10721-10726
pubmed: 33408950
Arch Biochem Biophys. 1986 Dec;251(2):440-9
pubmed: 3800377
ACS Chem Biol. 2016 Jul 15;11(7):1784-94
pubmed: 27176929
Chem Commun (Camb). 2012 Mar 11;48(21):2728-30
pubmed: 22306833
Bioorg Med Chem Lett. 2013 Jul 1;23(13):3764-8
pubmed: 23707255
Angew Chem Int Ed Engl. 2018 Jul 20;57(30):9268-9273
pubmed: 29732660
Chem Commun (Camb). 2017 Aug 10;53(65):9075-9077
pubmed: 28752167
Biochem Biophys Res Commun. 1970 May 11;39(3):371-8
pubmed: 5421939
Org Lett. 2008 Mar 6;10(5):1009-12
pubmed: 18254640
J Am Chem Soc. 2019 Apr 10;141(14):5581-5592
pubmed: 30888803
Carbohydr Res. 2015 Jun 26;411:1-5
pubmed: 25942062
Bioorg Med Chem. 2013 Aug 15;21(16):4778-85
pubmed: 23535562
Chemistry. 2010 Dec 3;16(45):13343-5
pubmed: 21031374
Nat Chem. 2016 Apr;8(4):338-46
pubmed: 27001729
Chem Commun (Camb). 2011 Oct 14;47(38):10815-7
pubmed: 21863157
Glycobiology. 2009 Feb;19(2):153-9
pubmed: 18955372
Front Chem. 2020 Jun 16;8:513
pubmed: 32612979
Science. 2013 Jul 26;341(6144):379-83
pubmed: 23888036
Angew Chem Int Ed Engl. 2008;47(7):1265-8
pubmed: 18172842
Nat Chem Biol. 2012 Sep;8(9):769-73
pubmed: 22820418
J Mol Biol. 2002 Apr 26;318(2):491-502
pubmed: 12051854
Mol Biosyst. 2009 Oct;5(10):1087-104
pubmed: 19756298
Adv Exp Med Biol. 1982;152:71-81
pubmed: 6814203
Appl Environ Microbiol. 2003 Apr;69(4):2110-5
pubmed: 12676690
Nat Chem Biol. 2018 Feb;14(2):156-162
pubmed: 29251719
Angew Chem Int Ed Engl. 2017 Sep 18;56(39):11784-11787
pubmed: 28731518

Auteurs

Xuan Fu (X)

Department of Chemistry, Georgia State University, Atlanta, GA, 30303, USA.
Center for Diagnostics & Therapeutics, Georgia State University, Atlanta, GA, 30303, USA.

Madhusudhan Reddy Gadi (MR)

Department of Chemistry, Georgia State University, Atlanta, GA, 30303, USA.

Shuaishuai Wang (S)

Department of Chemistry, Georgia State University, Atlanta, GA, 30303, USA.

Jinghua Han (J)

Department of Chemistry, Georgia State University, Atlanta, GA, 30303, USA.

Ding Liu (D)

Department of Chemistry, Georgia State University, Atlanta, GA, 30303, USA.

Xi Chen (X)

Department of Chemistry, University of California, Davis, Davis, CA, 95616, USA.

Jun Yin (J)

Department of Chemistry, Georgia State University, Atlanta, GA, 30303, USA.
Center for Diagnostics & Therapeutics, Georgia State University, Atlanta, GA, 30303, USA.

Lei Li (L)

Department of Chemistry, Georgia State University, Atlanta, GA, 30303, USA.

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Classifications MeSH