Synthesis of a Bifunctionalized Glycosylphosphatidylinositol (GPI) Anchor Useful for the Study of GPI Biology.
carbohydrate
click reaction
glycolipid
glycosylphosphatidylinositol
photoactivation
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
22 Mar 2023
22 Mar 2023
Historique:
received:
07
11
2022
pmc-release:
22
03
2024
pubmed:
30
11
2022
medline:
25
3
2023
entrez:
29
11
2022
Statut:
ppublish
Résumé
A new, bifunctional glycosylphosphatidylinositol (GPI) derivative containing the highly conserved core structure of all natural GPI anchors with a photoactivable diazirine in the lipid chain and clickable alkynes in the glycan was synthesized by a convergent [3+2] glycosylation strategy with late stage protecting group manipulation and regioselective phosphorylation. The challenges of this synthesis were due to the presence of several distinctive functional groups in the synthetic target, which complicated the protection tactics, in addition to the inherent difficulties associated with GPI synthesis. This bifunctional GPI derivative can cross-react with molecules in proximity upon photoactivation and be subsequently labeled with other molecular tags via click reaction. Therefore, it should be a valuable probe for biological studies of GPIs, such as analysis of GPI-interacting membrane proteins, and gaining insights into their functional mechanisms.
Identifiants
pubmed: 36445784
doi: 10.1002/chem.202203457
pmc: PMC10038835
mid: NIHMS1854446
doi:
Substances chimiques
Glycosylphosphatidylinositols
0
Membrane Proteins
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202203457Subventions
Organisme : NIGMS NIH HHS
ID : R35 GM131686
Pays : United States
Organisme : ODCDC CDC HHS
ID : S10 OD021758
Pays : United States
Informations de copyright
© 2022 Wiley-VCH GmbH.
Références
FEBS Lett. 2009 Nov 19;583(22):3671-5
pubmed: 19854187
Angew Chem Int Ed Engl. 2001 Jun 1;40(11):2004-2021
pubmed: 11433435
J Biol Chem. 1995 Mar 17;270(11):6088-99
pubmed: 7890742
J Biol Chem. 2011 Mar 18;286(11):8752-8
pubmed: 21212283
J Cell Sci. 1994 Jul;107 ( Pt 7):1783-96
pubmed: 7983148
J Biol Regul Homeost Agents. 2000 Apr-Jun;14(2):99-115
pubmed: 10841285
Angew Chem Int Ed Engl. 1998 Dec 31;37(24):3423-3428
pubmed: 29711276
Carbohydr Res. 1992 Nov 4;235:95-114
pubmed: 1473115
Biochem J. 1993 Sep 1;294 ( Pt 2):305-24
pubmed: 8373346
Cell. 2015 Apr 23;161(3):581-594
pubmed: 25910209
Chemistry. 2012 Jan 23;18(4):1194-201
pubmed: 22189835
Org Lett. 2019 Sep 6;21(17):6638-6642
pubmed: 31437002
Bioorg Med Chem. 2012 Jan 15;20(2):554-70
pubmed: 21778062
J Biol Chem. 1999 Oct 15;274(42):29862-73
pubmed: 10514467
Biochem J. 2010 Apr 28;428(1):95-101
pubmed: 20196773
Acc Chem Res. 2006 Apr;39(4):267-72
pubmed: 16618094
J Org Chem. 2022 Jul 15;87(14):9419-9425
pubmed: 35766889
Glycoconj J. 2000 Mar-Apr;17(3 -4):153-62
pubmed: 11201786
Angew Chem Int Ed Engl. 2011 Oct 10;50(42):9961-4
pubmed: 21898727
J Org Chem. 2001 Nov 2;66(22):7432-42
pubmed: 11681958
Annu Rev Biochem. 1988;57:285-320
pubmed: 3052274
Chem Sci. 2011;2(12):2342-2352
pubmed: 22163072
Biochemistry. 1990 Jun 12;29(23):5413-22
pubmed: 2143679
Angew Chem Int Ed Engl. 2006 Jan 9;45(3):468-74
pubmed: 16342127
J Am Chem Soc. 2003 Dec 31;125(52):16334-9
pubmed: 14692775
Chem Commun (Camb). 2005 Jan 28;(4):519-21
pubmed: 15654389
J Am Chem Soc. 2004 Jun 23;126(24):7540-7
pubmed: 15198601
Chem Rev. 2011 Aug 10;111(8):4405-17
pubmed: 21466226
ACS Chem Biol. 2021 Nov 19;16(11):2297-2306
pubmed: 34618440
Molecules. 2019 Jan 04;24(1):
pubmed: 30621193
J Am Chem Soc. 2010 May 19;132(19):6648-50
pubmed: 20423078