Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis

Lajos Z. Szabó, Dillon J. Hanrahan, Evan M. Jones, Erin Martin, Jeanne E Pemberton, Robin L Polt

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Here we report a method for the preparation of anomerically pure β-S-glycopyranosides (1,2-trans-glycosides) from the corresponding peracetate donors. S-glycosylation was performed in CHCl3 at reflux in the presence of a catalytic amount of InBr3. Deacylation of the intermediate peracetates were achieved under Zemplén conditions. Five pyranose examples, monosaccharides D-glucose and D-galactose and disaccharides cellobiose, maltose, and lactose, were used as donors, and five thiols including an α/ω dithiol and Fmoc-L-cysteine were used as acceptors. Melting points, high res MS, [α]D and NMR data (1H and 13C, including COSY, HSQC and HMBC) are reported for compounds not previously described.

Original languageEnglish (US)
Pages (from-to)1-4
Number of pages4
JournalCarbohydrate Research
Volume422
DOIs
StatePublished - Mar 3 2016

Fingerprint

Thioglycosides
Glycosylation
Cellobiose
Lewis Acids
Maltose
Monosaccharides
Disaccharides
Lactose
Glycosides
Catalysis
Galactose
Sulfhydryl Compounds
Surface-Active Agents
Freezing
Cysteine
Melting point
Nuclear magnetic resonance
Glucose
dithiol
indium bromide

Keywords

  • Glycolipid
  • Glycosylated cysteine
  • InBr
  • S-glycosidic linkage
  • Surfactant
  • Thioglycoside

ASJC Scopus subject areas

  • Biochemistry
  • Analytical Chemistry
  • Organic Chemistry

Cite this

Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis. / Szabó, Lajos Z.; Hanrahan, Dillon J.; Jones, Evan M.; Martin, Erin; Pemberton, Jeanne E; Polt, Robin L.

In: Carbohydrate Research, Vol. 422, 03.03.2016, p. 1-4.

Research output: Contribution to journalArticle

@article{9658a9327c834a9480a19f23553aee0d,
title = "Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis",
abstract = "Here we report a method for the preparation of anomerically pure β-S-glycopyranosides (1,2-trans-glycosides) from the corresponding peracetate donors. S-glycosylation was performed in CHCl3 at reflux in the presence of a catalytic amount of InBr3. Deacylation of the intermediate peracetates were achieved under Zempl{\'e}n conditions. Five pyranose examples, monosaccharides D-glucose and D-galactose and disaccharides cellobiose, maltose, and lactose, were used as donors, and five thiols including an α/ω dithiol and Fmoc-L-cysteine were used as acceptors. Melting points, high res MS, [α]D and NMR data (1H and 13C, including COSY, HSQC and HMBC) are reported for compounds not previously described.",
keywords = "Glycolipid, Glycosylated cysteine, InBr, S-glycosidic linkage, Surfactant, Thioglycoside",
author = "Szab{\'o}, {Lajos Z.} and Hanrahan, {Dillon J.} and Jones, {Evan M.} and Erin Martin and Pemberton, {Jeanne E} and Polt, {Robin L}",
year = "2016",
month = "3",
day = "3",
doi = "10.1016/j.carres.2015.12.008",
language = "English (US)",
volume = "422",
pages = "1--4",
journal = "Carbohydrate Research",
issn = "0008-6215",
publisher = "Elsevier BV",

}

TY - JOUR

T1 - Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis

AU - Szabó, Lajos Z.

AU - Hanrahan, Dillon J.

AU - Jones, Evan M.

AU - Martin, Erin

AU - Pemberton, Jeanne E

AU - Polt, Robin L

PY - 2016/3/3

Y1 - 2016/3/3

N2 - Here we report a method for the preparation of anomerically pure β-S-glycopyranosides (1,2-trans-glycosides) from the corresponding peracetate donors. S-glycosylation was performed in CHCl3 at reflux in the presence of a catalytic amount of InBr3. Deacylation of the intermediate peracetates were achieved under Zemplén conditions. Five pyranose examples, monosaccharides D-glucose and D-galactose and disaccharides cellobiose, maltose, and lactose, were used as donors, and five thiols including an α/ω dithiol and Fmoc-L-cysteine were used as acceptors. Melting points, high res MS, [α]D and NMR data (1H and 13C, including COSY, HSQC and HMBC) are reported for compounds not previously described.

AB - Here we report a method for the preparation of anomerically pure β-S-glycopyranosides (1,2-trans-glycosides) from the corresponding peracetate donors. S-glycosylation was performed in CHCl3 at reflux in the presence of a catalytic amount of InBr3. Deacylation of the intermediate peracetates were achieved under Zemplén conditions. Five pyranose examples, monosaccharides D-glucose and D-galactose and disaccharides cellobiose, maltose, and lactose, were used as donors, and five thiols including an α/ω dithiol and Fmoc-L-cysteine were used as acceptors. Melting points, high res MS, [α]D and NMR data (1H and 13C, including COSY, HSQC and HMBC) are reported for compounds not previously described.

KW - Glycolipid

KW - Glycosylated cysteine

KW - InBr

KW - S-glycosidic linkage

KW - Surfactant

KW - Thioglycoside

UR - http://www.scopus.com/inward/record.url?scp=84955455910&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84955455910&partnerID=8YFLogxK

U2 - 10.1016/j.carres.2015.12.008

DO - 10.1016/j.carres.2015.12.008

M3 - Article

VL - 422

SP - 1

EP - 4

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

ER -