7-Fluorosialyl Glycosides Are Hydrolysis Resistant but Readily Assembled by Sialyltransferases Providing Easy Access to More Metabolically Stable Glycoproteins.


Journal

ACS central science
ISSN: 2374-7943
Titre abrégé: ACS Cent Sci
Pays: United States
ID NLM: 101660035

Informations de publication

Date de publication:
24 Feb 2021
Historique:
received: 24 11 2020
entrez: 3 3 2021
pubmed: 4 3 2021
medline: 4 3 2021
Statut: ppublish

Résumé

The maintenance of therapeutic glycoproteins within the circulatory system is associated, in large part, with the integrity of sialic acids as terminal sugars on the glycans. Glycoprotein desialylation, either by spontaneous cleavage or through host sialidases, leads to protein clearance, mainly through the liver. Thus, the installation of minimally modified sialic acids that are hydrolysis-resistant yet biologically equivalent should lead to increased circulatory half-lives and improved pharmacokinetic profiles. Here we describe the chemoenzymatic synthesis of CMP-sialic acid sugar donors bearing fluorine atoms at the 7-position, starting from the corresponding 4-deoxy-4-fluoro-

Identifiants

pubmed: 33655072
doi: 10.1021/acscentsci.0c01589
pmc: PMC7908025
doi:

Types de publication

Journal Article

Langues

eng

Pagination

345-354

Informations de copyright

© 2021 American Chemical Society.

Déclaration de conflit d'intérêts

The authors declare the following competing financial interest(s): We hold an issued patent on the technology.

Références

Glycobiology. 1997 Jun;7(4):559-63
pubmed: 9184837
Proc Natl Acad Sci U S A. 2015 Nov 3;112(44):13657-62
pubmed: 26489654
J Am Chem Soc. 2005 Dec 21;127(50):17618-9
pubmed: 16351087
Biochemistry. 2007 Jun 19;46(24):7196-204
pubmed: 17518445
Nat Biotechnol. 2018 Dec 6;36(12):1136-1145
pubmed: 30520869
J Mol Biol. 1993 Aug 20;232(4):1069-83
pubmed: 8371267
Proteomics. 2006 Jun;6(11):3369-80
pubmed: 16622833
Carbohydr Res. 1990 May 1;198(2):205-21
pubmed: 2379186
J Biol Chem. 2005 Jan 7;280(1):469-75
pubmed: 15501818
Chem Rev. 2009 Jan;109(1):131-63
pubmed: 19093879
J Am Chem Soc. 2019 Apr 24;141(16):6484-6488
pubmed: 30969765
J Biochem. 2008 Feb;143(2):187-97
pubmed: 17984122
Biochemistry. 2007 May 29;46(21):6288-98
pubmed: 17487984
J Am Chem Soc. 2007 Sep 5;129(35):10630-1
pubmed: 17696347
Nat Rev Dis Primers. 2016 Jul 28;2:16051
pubmed: 27465791
Bioorg Med Chem Lett. 2001 Jan 22;11(2):141-4
pubmed: 11206445
J Biol Chem. 2016 Sep 2;291(36):18700-17
pubmed: 27405760
J Am Chem Soc. 2010 Jul 14;132(27):9430-7
pubmed: 20557044
Chemistry. 2006 Jan 11;12(3):845-58
pubmed: 16196067
Curr Med Res Opin. 2009 Apr;25(4):991-1002
pubmed: 19275518
Proc Natl Acad Sci U S A. 2005 Nov 22;102(47):17125-9
pubmed: 16286643
J Biol Chem. 1971 Mar 10;246(5):1461-7
pubmed: 5545089
Biotechnol Appl Biochem. 2018 May;65(3):306-322
pubmed: 28972297
Curr Opin Chem Biol. 2004 Dec;8(6):617-25
pubmed: 15556405
Curr Opin Chem Biol. 2008 Oct;12(5):565-72
pubmed: 18625334
Cell Chem Biol. 2019 Feb 21;26(2):203-212.e5
pubmed: 30503285
Clin Chest Med. 2014 Mar;35(1):39-50
pubmed: 24507836
Org Biomol Chem. 2006 Dec 21;4(24):4453-9
pubmed: 17268638
Front Oncol. 2018 Jun 04;8:163
pubmed: 29915719
J Biol Chem. 1995 Mar 31;270(13):7523-32
pubmed: 7706299
N Engl J Med. 2005 Jan 13;352(2):174-83
pubmed: 15647580
Carbohydr Res. 2008 Aug 11;343(12):2075-82
pubmed: 18353292
J Pharm Sci. 2009 Apr;98(4):1223-45
pubmed: 18661536
Respir Care. 2018 Jun;63(6):690-698
pubmed: 29794204
Trends Pharmacol Sci. 2010 Feb;31(2):53-9
pubmed: 19963283
Anal Biochem. 1994 Jul;220(1):92-7
pubmed: 7978262
Appl Microbiol Biotechnol. 2008 Oct;80(5):757-65
pubmed: 18716769
Eur J Clin Pharmacol. 2010 Apr;66(4):331-40
pubmed: 20127232
Nat Struct Mol Biol. 2004 Feb;11(2):163-70
pubmed: 14730352
J Biol Chem. 2009 Jun 26;284(26):17404-10
pubmed: 19411257
Proc Natl Acad Sci U S A. 2011 May 3;108(18):7397-402
pubmed: 21502532
Chem Rev. 2016 Dec 14;116(23):14277-14306
pubmed: 27960262
J Biol Chem. 2008 Apr 4;283(14):9080-8
pubmed: 18218621
Protein Expr Purif. 2002 Jul;25(2):237-40
pubmed: 12135555
Mol Pharm. 2013 Jul 1;10(7):2616-29
pubmed: 23668542
J Biol Chem. 2004 Sep 24;279(39):40954-9
pubmed: 15262963
Org Biomol Chem. 2009 May 7;7(9):1778-80
pubmed: 19590770
Glycoconj J. 1994 Apr;11(2):141-51
pubmed: 7804004
Carbohydr Res. 2014 May 7;389:100-11
pubmed: 24680514
J Biol Chem. 2001 Apr 20;276(16):12624-8
pubmed: 11278827
J Biol Chem. 2006 Feb 17;281(7):4149-55
pubmed: 16298994
J Am Chem Soc. 2008 Jul 2;130(26):8169-71
pubmed: 18529007
Org Biomol Chem. 2009 Dec 21;7(24):5137-45
pubmed: 20024109
Crit Rev Biotechnol. 2014 Dec;34(4):281-99
pubmed: 23919242

Auteurs

Andreas Geissner (A)

Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada.

Lars Baumann (L)

Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada.

Thomas J Morley (TJ)

Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada.

Andrew K O Wong (AKO)

Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada.

Lyann Sim (L)

Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada.

Jamie R Rich (JR)

Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada.

Pauline P L So (PPL)

AdMare BioInnovations, 2405 Wesbrook Mall, Vancouver, BC V6T 1Z3, Canada.

Edie M Dullaghan (EM)

AdMare BioInnovations, 2405 Wesbrook Mall, Vancouver, BC V6T 1Z3, Canada.

Etienne Lessard (E)

National Research Council Canada, Human Health Therapeutics, Ottawa, ON K1A 0R6, Canada.

Umar Iqbal (U)

National Research Council Canada, Human Health Therapeutics, Ottawa, ON K1A 0R6, Canada.

Maria Moreno (M)

National Research Council Canada, Human Health Therapeutics, Ottawa, ON K1A 0R6, Canada.

Warren W Wakarchuk (WW)

Department of Biological Sciences, University of Alberta, Edmonton, AB T6G 2E9, Canada.

Stephen G Withers (SG)

Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada.

Classifications MeSH