Step-economy synthesis of β-steryl sialosides using a sialyl iodide donor

Simon S. Park, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticle

Abstract

Steryl glycosides are prevalent in nature and have unique biological activities dictated by sterol structure, sugar composition, and the stereochemical attachment of the aglycone. A single configurational switch can have profound biological consequences meriting the systematic study of structure and function relationships. Steryl congeners of N-acetyl neuraminic acid (NANA) impact neurobiological processes and may also mediate host/microbe interactions. In order to study these processes, a platform for the synthesis of β-steryl sialosides has been established. Promoter-free glycosidations using a novel α-linked sialyl iodide donor efficiently provide unique amphiphilic sialoglycoconjugates for examining bioactivities in various systems.

Original languageEnglish (US)
Pages (from-to)449-460
Number of pages12
JournalJournal of Antibiotics
Volume72
Issue number6
DOIs
StatePublished - Jun 1 2019

Fingerprint

Neuraminic Acids
Iodides
Sterols
Glycosides

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

Cite this

Step-economy synthesis of β-steryl sialosides using a sialyl iodide donor. / Park, Simon S.; Gervay-Hague, Jacquelyn.

In: Journal of Antibiotics, Vol. 72, No. 6, 01.06.2019, p. 449-460.

Research output: Contribution to journalArticle

@article{aafdf15b61e849f2af4d67a926deeb38,
title = "Step-economy synthesis of β-steryl sialosides using a sialyl iodide donor",
abstract = "Steryl glycosides are prevalent in nature and have unique biological activities dictated by sterol structure, sugar composition, and the stereochemical attachment of the aglycone. A single configurational switch can have profound biological consequences meriting the systematic study of structure and function relationships. Steryl congeners of N-acetyl neuraminic acid (NANA) impact neurobiological processes and may also mediate host/microbe interactions. In order to study these processes, a platform for the synthesis of β-steryl sialosides has been established. Promoter-free glycosidations using a novel α-linked sialyl iodide donor efficiently provide unique amphiphilic sialoglycoconjugates for examining bioactivities in various systems.",
author = "Park, {Simon S.} and Jacquelyn Gervay-Hague",
year = "2019",
month = "6",
day = "1",
doi = "10.1038/s41429-019-0165-0",
language = "English (US)",
volume = "72",
pages = "449--460",
journal = "Journal of Antibiotics",
issn = "0021-8820",
publisher = "Japan Antibiotics Research Association",
number = "6",

}

TY - JOUR

T1 - Step-economy synthesis of β-steryl sialosides using a sialyl iodide donor

AU - Park, Simon S.

AU - Gervay-Hague, Jacquelyn

PY - 2019/6/1

Y1 - 2019/6/1

N2 - Steryl glycosides are prevalent in nature and have unique biological activities dictated by sterol structure, sugar composition, and the stereochemical attachment of the aglycone. A single configurational switch can have profound biological consequences meriting the systematic study of structure and function relationships. Steryl congeners of N-acetyl neuraminic acid (NANA) impact neurobiological processes and may also mediate host/microbe interactions. In order to study these processes, a platform for the synthesis of β-steryl sialosides has been established. Promoter-free glycosidations using a novel α-linked sialyl iodide donor efficiently provide unique amphiphilic sialoglycoconjugates for examining bioactivities in various systems.

AB - Steryl glycosides are prevalent in nature and have unique biological activities dictated by sterol structure, sugar composition, and the stereochemical attachment of the aglycone. A single configurational switch can have profound biological consequences meriting the systematic study of structure and function relationships. Steryl congeners of N-acetyl neuraminic acid (NANA) impact neurobiological processes and may also mediate host/microbe interactions. In order to study these processes, a platform for the synthesis of β-steryl sialosides has been established. Promoter-free glycosidations using a novel α-linked sialyl iodide donor efficiently provide unique amphiphilic sialoglycoconjugates for examining bioactivities in various systems.

UR - http://www.scopus.com/inward/record.url?scp=85064917675&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85064917675&partnerID=8YFLogxK

U2 - 10.1038/s41429-019-0165-0

DO - 10.1038/s41429-019-0165-0

M3 - Article

C2 - 30886347

AN - SCOPUS:85064917675

VL - 72

SP - 449

EP - 460

JO - Journal of Antibiotics

JF - Journal of Antibiotics

SN - 0021-8820

IS - 6

ER -