Design, Synthesis, and Characterization of Stapled Oligosaccharides.
Journal
Journal of the American Chemical Society
ISSN: 1520-5126
Titre abrégé: J Am Chem Soc
Pays: United States
ID NLM: 7503056
Informations de publication
Date de publication:
12 10 2022
12 10 2022
Historique:
pubmed:
30
9
2022
medline:
14
10
2022
entrez:
29
9
2022
Statut:
ppublish
Résumé
Stapling short peptides to lock specific conformations and thereby obtain superior pharmacological properties is well established. However, similar concepts have not been applied to oligosaccharides. Here, we describe the design, synthesis, and characterization of the first stapled oligosaccharides. Automated assembly of β-(1,6)-glucans equipped with two alkenyl side chains was followed by on-resin Grubbs metathesis for efficient ring closure with a variety of cross-linkers of different sizes. Oligosaccharide stapling increases enzymatic stability and cell penetration, therefore opening new opportunities for the use of glycans in medicinal chemistry.
Identifiants
pubmed: 36173281
doi: 10.1021/jacs.2c06882
pmc: PMC9562281
doi:
Substances chimiques
Glucans
0
Oligosaccharides
0
Peptides
0
Polysaccharides
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
18429-18434Références
Nat Chem Biol. 2009 Nov;5(11):789-96
pubmed: 19841628
Drug Discov Today Technol. 2012 Spring;9(1):e1-e70
pubmed: 24064240
Chem Rev. 2019 Sep 11;119(17):9836-9860
pubmed: 30990310
Angew Chem Int Ed Engl. 2018 Oct 26;57(44):14414-14438
pubmed: 30144240
Eur J Med Chem. 2015 Apr 13;94:459-70
pubmed: 25591543
Chem Rev. 2019 Sep 11;119(17):10241-10287
pubmed: 31083977
Nat Protoc. 2011 Jun;6(6):761-71
pubmed: 21637196
Nature. 2006 Mar 16;440(7082):297-302
pubmed: 16541064
Angew Chem Int Ed Engl. 2015 Jul 27;54(31):8896-927
pubmed: 26119925
J Med Chem. 2022 Feb 24;65(4):3026-3045
pubmed: 35112864
Angew Chem Int Ed Engl. 2022 Jun 13;61(24):e202203239
pubmed: 35383396
Peptides. 2001 Dec;22(12):2329-43
pubmed: 11786210
Pharmaceuticals (Basel). 2020 Sep 29;13(10):
pubmed: 33003610
J Am Chem Soc. 2021 Jun 16;143(23):8893-8901
pubmed: 34060822
J Am Chem Soc. 2005 Mar 9;127(9):2974-83
pubmed: 15740134
Chem Rev. 2014 Aug 13;114(15):7678-739
pubmed: 25007213
Curr Opin Chem Biol. 2008 Dec;12(6):692-7
pubmed: 18793750
Glycobiology. 2016 Aug;26(8):788
pubmed: 27496763
J Am Chem Soc. 2022 Feb 2;144(4):1941-1950
pubmed: 35041415
Angew Chem Int Ed Engl. 2014 Nov 24;53(48):13020-41
pubmed: 25287434
Adv Drug Deliv Rev. 2001 Mar 1;46(1-3):3-26
pubmed: 11259830
Drug Discov Today Technol. 2012 Spring;9(1):e1-e70
pubmed: 24064243
Science. 2004 Sep 3;305(5689):1466-70
pubmed: 15353804
J Am Chem Soc. 2018 Apr 25;140(16):5421-5426
pubmed: 29624385
J Med Chem. 2014 Aug 14;57(15):6275-88
pubmed: 24601557
J Am Chem Soc. 2002 May 29;124(21):5964-73
pubmed: 12022829
Biomacromolecules. 2020 Jan 13;21(1):18-29
pubmed: 31517479
Chem Rev. 2020 Sep 23;120(18):10079-10144
pubmed: 32794722
Nat Rev Genet. 2006 Jul;7(7):565-75
pubmed: 16770339
J Am Chem Soc. 2012 Oct 24;134(42):17704-13
pubmed: 22998171
Nat Prod Rep. 2018 Mar 1;35(3):220-229
pubmed: 29513338
ACS Chem Biol. 2015 Jun 19;10(6):1362-75
pubmed: 25798993