On-Chip Neo-Glycopeptide Synthesis for Multivalent Glycan Presentation.
click chemistry
combinatorial chemistry
laser-induced forward transfer
lectin
microarrays
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
06 Aug 2020
06 Aug 2020
Historique:
received:
15
03
2020
revised:
17
04
2020
pubmed:
22
4
2020
medline:
3
3
2021
entrez:
22
4
2020
Statut:
ppublish
Résumé
Single glycan-protein interactions are often weak, such that glycan binding partners commonly utilize multiple, spatially defined binding sites to enhance binding avidity and specificity. Current array technologies usually neglect defined multivalent display. Laser-based array synthesis technology allows for flexible and rapid on-surface synthesis of different peptides. By combining this technique with click chemistry, neo-glycopeptides were produced directly on a functionalized glass slide in the microarray format. Density and spatial distribution of carbohydrates can be tuned, resulting in well-defined glycan structures for multivalent display. The two lectins concanavalin A and langerin were probed with different glycans on multivalent scaffolds, revealing strong spacing-, density-, and ligand-dependent binding. In addition, we could also measure the surface dissociation constant. This approach allows for a rapid generation, screening, and optimization of a multitude of multivalent scaffolds for glycan binding.
Identifiants
pubmed: 32315099
doi: 10.1002/chem.202001291
pmc: PMC7496964
doi:
Substances chimiques
Glycopeptides
0
Polysaccharides
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
9954-9963Subventions
Organisme : Bundesministerium für Bildung und Forschung
ID : 13XP5050A
Organisme : Max-Planck-Gesellschaft
ID : Glyco3Display
Informations de copyright
© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
Références
J Am Chem Soc. 2010 Jul 28;132(29):9963-5
pubmed: 20608651
Org Lett. 2003 May 29;5(11):1951-4
pubmed: 12762694
Org Biomol Chem. 2009 May 21;7(10):2013-25
pubmed: 19421435
Angew Chem Int Ed Engl. 2018 Nov 5;57(45):14873-14877
pubmed: 30216608
Chem Rev. 2002 Feb;102(2):555-78
pubmed: 11841254
Glycobiology. 2005 Jan;15(1):31-41
pubmed: 15342550
Chemistry. 2008;14(25):7490-9
pubmed: 18618537
Chembiochem. 2008 Jul 21;9(11):1836-44
pubmed: 18604837
Chem Commun (Camb). 2010 Jan 7;46(1):21-43
pubmed: 20024291
Chem Commun (Camb). 2011 Sep 7;47(33):9321-3
pubmed: 21785785
Anal Chem. 2012 Apr 3;84(7):3330-8
pubmed: 22390135
Angew Chem Int Ed Engl. 2012 Oct 15;51(42):10472-98
pubmed: 22952048
Annu Rev Biochem. 2011;80:797-823
pubmed: 21469953
Chem Sci. 2014 May 1;5(5):2023-2030
pubmed: 34113434
Chem Rev. 2016 Feb 24;116(4):1693-752
pubmed: 26702928
ACS Chem Biol. 2015 May 15;10(5):1290-302
pubmed: 25664929
Chembiochem. 2005 Dec;6(12):2229-41
pubmed: 16252298
Curr Opin Chem Biol. 2014 Feb;18:38-45
pubmed: 24534751
RSC Adv. 2018 Apr 19;8(27):14898-14905
pubmed: 35541319
Faraday Discuss. 2019 Oct 30;219(0):9-32
pubmed: 31298252
J Proteome Res. 2009 Nov;8(11):5031-40
pubmed: 19791771
Glycobiology. 2005 Jul;15(7):700-8
pubmed: 15716466
Chembiochem. 2010 Sep 3;11(13):1896-904
pubmed: 20672284
J Carbohydr Chem. 2012 Jan 1;31(4-6):466-503
pubmed: 23519474
Nat Commun. 2016 Jun 14;7:11844
pubmed: 27296868
Chemistry. 2013 Feb 25;19(9):3090-8
pubmed: 23325532
Beilstein J Org Chem. 2013 Nov 07;9:2395-403
pubmed: 24367405
Glycobiology. 2008 Oct;18(10):789-98
pubmed: 18633134
Immunopharmacol Immunotoxicol. 2010 Jun;32(2):196-207
pubmed: 20141495
Chemistry. 2020 Aug 6;26(44):9954-9963
pubmed: 32315099
Glycobiology. 2014 Jun;24(6):507-17
pubmed: 24658466
Curr Opin Biotechnol. 2018 Jun;51:24-31
pubmed: 29175707
J Am Chem Soc. 2003 May 21;125(20):6140-8
pubmed: 12785845
Angew Chem Int Ed Engl. 2008;47(18):3396-9
pubmed: 18383458
J Am Chem Soc. 2010 Jul 21;132(28):9653-62
pubmed: 20583754
Chem Soc Rev. 2013 Jun 7;42(11):4518-31
pubmed: 22911174
Chem Commun (Camb). 2010 Dec 28;46(48):9119-21
pubmed: 21038043
J Biol Chem. 2010 Apr 23;285(17):13285-93
pubmed: 20181944
Angew Chem Int Ed Engl. 2015 Jun 15;54(25):7436-40
pubmed: 25940402
Langmuir. 2008 Aug 5;24(15):8151-7
pubmed: 18605707
Angew Chem Int Ed Engl. 2003 Nov 10;42(43):5317-20
pubmed: 14613164
Chembiochem. 2009 May 25;10(8):1369-78
pubmed: 19405074
Angew Chem Int Ed Engl. 2006 May 26;45(22):3607-10
pubmed: 16639753
J Am Chem Soc. 2014 Feb 5;136(5):2008-16
pubmed: 24417254
J Biol Chem. 2017 Jan 20;292(3):862-871
pubmed: 27903635
Proteomics. 2002 Dec;2(12):1666-71
pubmed: 12469336
Angew Chem Int Ed Engl. 2009;48(27):4973-6
pubmed: 19479916
Chembiochem. 2011 Jan 3;12(1):56-60
pubmed: 21154493
J Am Chem Soc. 2017 Mar 22;139(11):4157-4167
pubmed: 28234007
Science. 2013 Jul 26;341(6144):379-83
pubmed: 23888036
Faraday Discuss. 2019 Oct 30;219(0):203-219
pubmed: 31314021
Chemistry. 2006 Jan 11;12(3):656-65
pubmed: 16187378
Faraday Discuss. 2019 Oct 30;219(0):90-111
pubmed: 31338503
Angew Chem Int Ed Engl. 2009;48(41):7695-700
pubmed: 19774579
J Am Chem Soc. 2012 Sep 26;134(38):15732-42
pubmed: 22967056
Plant Physiol. 2017 Nov;175(3):1094-1104
pubmed: 28924016
Nat Biotechnol. 2002 Mar;20(3):275-81
pubmed: 11875429
Nature. 2000 Feb 10;403(6770):669-72
pubmed: 10688205
Chem Asian J. 2012 Sep;7(9):2052-60
pubmed: 22615235
ACS Cent Sci. 2019 May 22;5(5):808-820
pubmed: 31139717
Sensors (Basel). 2017 Aug 15;17(8):
pubmed: 28809819
J Am Chem Soc. 2007 Sep 12;129(36):11177-84
pubmed: 17705486
Angew Chem Int Ed Engl. 2000 Dec 1;39(23):4348-4352
pubmed: 29711903
Annu Rev Anal Chem (Palo Alto Calif). 2016 Jun 12;9(1):223-47
pubmed: 27306309
Small. 2012 Jul 9;8(13):2000-5
pubmed: 22488791
Glycoconj J. 2008 Jan;25(1):75-84
pubmed: 18193481
Biomacromolecules. 2012 Jun 11;13(6):1845-52
pubmed: 22483345
Faraday Discuss. 2019 Oct 30;219(0):77-89
pubmed: 31364656