Differential Labeling of Glycoproteins with Alkynyl Fucose Analogs.


Journal

International journal of molecular sciences
ISSN: 1422-0067
Titre abrégé: Int J Mol Sci
Pays: Switzerland
ID NLM: 101092791

Informations de publication

Date de publication:
20 Aug 2020
Historique:
received: 29 07 2020
revised: 12 08 2020
accepted: 18 08 2020
entrez: 23 8 2020
pubmed: 23 8 2020
medline: 14 4 2021
Statut: epublish

Résumé

Fucosylated glycans critically regulate the physiological functions of proteins and cells. Alterations in levels of fucosylated glycans are associated with various diseases. For detection and functional modulation of fucosylated glycans, chemical biology approaches using fucose (Fuc) analogs are useful. However, little is known about how efficiently each unnatural Fuc analog is utilized by enzymes in the biosynthetic pathway of fucosylated glycans. We show here that three clickable Fuc analogs with similar but distinct structures labeled cellular glycans with different efficiency and protein specificity. For instance, 6-alkynyl (Alk)-Fuc modified

Identifiants

pubmed: 32825463
pii: ijms21176007
doi: 10.3390/ijms21176007
pmc: PMC7503990
pii:
doi:

Substances chimiques

Glycoproteins 0
Polysaccharides 0
Recombinant Proteins 0
Thrombospondin 1 0
thrombospondin-1, human 0
Guanosine Diphosphate 146-91-8
Fucose 28RYY2IV3F
Fucosyltransferases EC 2.4.1.-
polypeptide fucosyltransferase EC 2.4.1.221
3-galactosyl-N-acetylglucosaminide 4-alpha-L-fucosyltransferase EC 2.4.1.65

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Subventions

Organisme : Tokyo Biochemical Research Foundation
ID : YK
Organisme : NIGMS NIH HHS
ID : GM061126
Pays : United States
Organisme : Japan Society for the Promotion of Science
ID : JP19H03176
Organisme : Japan Society for the Promotion of Science
ID : 16811705
Organisme : Japan Agency for Medical Research and Development
ID : 16809274
Organisme : Takeda Science Foundation
ID : YK
Organisme : Japan Society for the Promotion of Science
ID : JP19H03416
Organisme : Japan Society for the Promotion of Science
ID : JP19KK0195
Organisme : Japan Society for the Promotion of Science
ID : JP20H03207
Organisme : NIGMS NIH HHS
ID : R01 GM061126
Pays : United States
Organisme : Takeda Science Foundation
ID : HT

Références

Glycobiology. 2010 Jul;20(7):865-71
pubmed: 20371511
J Biol Chem. 2010 Feb 5;285(6):4122-9
pubmed: 19948734
J Immunol. 2015 Mar 15;194(6):2596-606
pubmed: 25694612
Dev Growth Differ. 2020 Jan;62(1):35-48
pubmed: 31886522
Nat Chem Biol. 2018 Jan;14(1):65-71
pubmed: 29176671
J Biol Chem. 2015 Jun 12;290(24):15313-26
pubmed: 25944902
Glycobiology. 2017 Aug 1;27(8):777-786
pubmed: 28334865
Acta Crystallogr D Biol Crystallogr. 2004 Dec;60(Pt 12 Pt 1):2256-68
pubmed: 15572779
Nat Chem Biol. 2012 Jul;8(7):661-8
pubmed: 22683610
Adv Cancer Res. 2015;126:11-51
pubmed: 25727145
J Biol Chem. 2020 May 8;295(19):6677-6688
pubmed: 32220931
EMBO J. 2012 Jul 18;31(14):3183-97
pubmed: 22588082
Curr Opin Cell Biol. 1994 Oct;6(5):663-73
pubmed: 7530461
J Biol Chem. 2020 Jun 5;295(23):7992-8004
pubmed: 32350116
Nat Rev Immunol. 2004 May;4(5):325-35
pubmed: 15122198
Gastroenterology. 2016 Jun;150(7):1620-1632
pubmed: 26965517
Proc Natl Acad Sci U S A. 2013 Apr 2;110(14):5404-9
pubmed: 23493549
Nat Med. 2000 Mar;6(3):306-12
pubmed: 10700233
J Biol Chem. 2005 Dec 23;280(51):42454-63
pubmed: 16221665
J Biol Chem. 2012 Oct 5;287(41):33934-44
pubmed: 22872643
Glycobiology. 2003 Jul;13(7):41R-53R
pubmed: 12651883
Nat Chem Biol. 2017 Jul;13(7):757-763
pubmed: 28530709
Nat Commun. 2020 Feb 20;11(1):973
pubmed: 32080177
Oncol Lett. 2019 Mar;17(3):2569-2575
pubmed: 30854032
Cell Chem Biol. 2017 Dec 21;24(12):1467-1478.e5
pubmed: 29033318
Proc Natl Acad Sci U S A. 2006 Aug 15;103(33):12371-6
pubmed: 16895981
Glycobiology. 2012 Jun;22(6):736-56
pubmed: 22183981
FEBS Lett. 2019 Jul;593(13):1598-1615
pubmed: 31215021
Glycobiology. 2013 Feb;23(2):188-98
pubmed: 23045360
Dev Biol. 2010 Oct 1;346(1):25-38
pubmed: 20637190
Angew Chem Int Ed Engl. 2009;48(22):4030-3
pubmed: 19388017
J Biol Chem. 2005 Jul 22;280(29):27230-5
pubmed: 15911612
Chem Commun (Camb). 2013 Dec 14;49(96):11293-5
pubmed: 24153356
Proc Natl Acad Sci U S A. 2009 Jan 6;106(1):12-7
pubmed: 19104067
J Am Chem Soc. 2006 Sep 20;128(37):12078-9
pubmed: 16967952
J Biol Chem. 2012 Nov 16;287(47):40021-30
pubmed: 23019334
Bioconjug Chem. 2014 Apr 16;25(4):698-706
pubmed: 24499412
Comput Struct Biotechnol J. 2014 Jun 11;10(16):23-32
pubmed: 25210595
J Biol Chem. 2006 Apr 7;281(14):9393-9
pubmed: 16464857
Am J Hum Genet. 2013 Jun 6;92(6):895-903
pubmed: 23684010
Proc Natl Acad Sci U S A. 2005 Nov 1;102(44):15791-6
pubmed: 16236725
Proc Natl Acad Sci U S A. 2011 May 17;108(20):8146-51
pubmed: 21540332
Glycobiology. 2018 May 1;28(5):276-283
pubmed: 29452367
Glycobiology. 2017 Jul 1;27(7):601-618
pubmed: 28430973
Cell. 2006 Sep 8;126(5):855-67
pubmed: 16959566
Biochem Biophys Res Commun. 2016 Apr 29;473(2):503-10
pubmed: 27003260
Cell Chem Biol. 2016 Jul 21;23(7):782-792
pubmed: 27447047
J Biol Chem. 2010 Nov 12;285(46):36245-54
pubmed: 20837470
Cancer Cell. 2017 Jun 12;31(6):804-819.e7
pubmed: 28609658
Nat Chem Biol. 2019 Sep;15(9):853-864
pubmed: 31427814
Immunity. 2001 Jul;15(1):115-26
pubmed: 11485743
J Biol Chem. 2005 Mar 25;280(12):11289-94
pubmed: 15653671
Mol Cell Proteomics. 2019 Oct;18(10):2044-2057
pubmed: 31375533
Cells. 2020 May 14;9(5):
pubmed: 32423029
Proc Natl Acad Sci U S A. 2007 Feb 20;104(8):2614-9
pubmed: 17296930
J Biol Chem. 2003 Jan 31;278(5):3466-73
pubmed: 12427744
J Biol Chem. 2011 May 27;286(21):18434-43
pubmed: 21471224
Nat Rev Cancer. 2015 Sep;15(9):540-55
pubmed: 26289314
Proc Natl Acad Sci U S A. 2003 Apr 29;100(9):5234-9
pubmed: 12697902
ACS Chem Biol. 2016 Oct 21;11(10):2734-2743
pubmed: 27434622
J Biol Chem. 2006 Apr 7;281(14):9385-92
pubmed: 16464858
Curr Opin Struct Biol. 2019 Jun;56:78-86
pubmed: 30690220
J Biol Chem. 2002 Jul 26;277(30):26733-40
pubmed: 11986321
Anal Biochem. 2014 Mar 1;448:14-22
pubmed: 24299991
Nat Med. 2011 Aug 14;17(9):1067-75
pubmed: 21841783
Methods Mol Biol. 2014;1187:209-21
pubmed: 25053492
Dev Biol. 2016 Aug 1;416(1):111-122
pubmed: 27297885
EMBO Mol Med. 2015 Jan 15;7(2):175-89
pubmed: 25592972
Nat Rev Mol Cell Biol. 2012 Jun 22;13(7):448-62
pubmed: 22722607
J Biol Chem. 2011 Sep 9;286(36):31623-37
pubmed: 21757702
Glycobiology. 2017 Jan;27(1):3-49
pubmed: 27558841

Auteurs

Chenyu Ma (C)

Department of Molecular Biochemistry, Nagoya University Graduate School of Medicine, Showa-ku, Nagoya 466-8550, Japan.

Hideyuki Takeuchi (H)

Department of Molecular Biochemistry, Nagoya University Graduate School of Medicine, Showa-ku, Nagoya 466-8550, Japan.
Institute for Glyco-core Research (iGCORE), Nagoya University, Chikusa-ku, Nagoya 464-8601, Japan.

Huilin Hao (H)

Complex Carbohydrate Research Center, Department of Biochemistry and Molecular Biology, University of Georgia, Athens, GA 30602, USA.

Chizuko Yonekawa (C)

Center for Highly Advanced Integration of Nano and Life Sciences (G-CHAIN), Gifu University, Gifu 501-1193, Japan.

Kazuki Nakajima (K)

Center for Research Promotion and Support, Fujita Health University, Toyoake 470-1192, Japan.

Masamichi Nagae (M)

Department of Molecular Immunology, Research Institute for Microbial Disease, Osaka University, Suita 565-0871, Japan.
Laboratory of Molecular Immunology, Immunology Frontier Research Center (IFReC), Osaka University, Suita 565-0871, Japan.

Tetsuya Okajima (T)

Department of Molecular Biochemistry, Nagoya University Graduate School of Medicine, Showa-ku, Nagoya 466-8550, Japan.
Institute for Glyco-core Research (iGCORE), Nagoya University, Chikusa-ku, Nagoya 464-8601, Japan.

Robert S Haltiwanger (RS)

Complex Carbohydrate Research Center, Department of Biochemistry and Molecular Biology, University of Georgia, Athens, GA 30602, USA.

Yasuhiko Kizuka (Y)

Center for Highly Advanced Integration of Nano and Life Sciences (G-CHAIN), Gifu University, Gifu 501-1193, Japan.
Institute for Glyco-core Research (iGCORE), Gifu University, Gifu 501-1193, Japan.

Articles similaires

[Redispensing of expensive oral anticancer medicines: a practical application].

Lisanne N van Merendonk, Kübra Akgöl, Bastiaan Nuijen
1.00
Humans Antineoplastic Agents Administration, Oral Drug Costs Counterfeit Drugs

Smoking Cessation and Incident Cardiovascular Disease.

Jun Hwan Cho, Seung Yong Shin, Hoseob Kim et al.
1.00
Humans Male Smoking Cessation Cardiovascular Diseases Female
Humans United States Aged Cross-Sectional Studies Medicare Part C
1.00
Humans Yoga Low Back Pain Female Male

Classifications MeSH