TMS Triflate‐Promoted O‐Glycosylation of Amino Acids and Peptides by L‐Acosaminal and L‐Ristosaminal

Horst Kessler; Katja Michael; Matthias Kottenhahn

doi:10.1002/jlac.199419940809

TMS Triflate‐Promoted O‐Glycosylation of Amino Acids and Peptides by L‐Acosaminal and L‐Ristosaminal

Horst Kessler
, Katja Michael
, Matthias Kottenhahn

TUM Emeriti of Excellence

Technical University of Munich
Evonik Industries AG

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

Cyclic and linear peptides are stereoselectively O‐glycosylated by 3‐(acylamino)glycals through activation with TMS triflate (trimethylsilyl trifluoromethanesulfonate) without Ferrier rearrangement. The yields of the 2‐deoxy‐α‐O‐glycosides obtained range from 18 to 95%. (Formula Presented.)

Original language	English
Pages (from-to)	811-816
Number of pages	6
Journal	Liebigs Annalen der Chemie
Volume	1994
Issue number	8
DOIs	https://doi.org/10.1002/jlac.199419940809
State	Published - 1994

Keywords

Amino acids
Carbohydrates
Glycopeptides
Glycosides
Glycosylations
Peptides

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10.1002/jlac.199419940809

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title = "TMS Triflate‐Promoted O‐Glycosylation of Amino Acids and Peptides by L‐Acosaminal and L‐Ristosaminal",

abstract = "Cyclic and linear peptides are stereoselectively O‐glycosylated by 3‐(acylamino)glycals through activation with TMS triflate (trimethylsilyl trifluoromethanesulfonate) without Ferrier rearrangement. The yields of the 2‐deoxy‐α‐O‐glycosides obtained range from 18 to 95\%. (Formula Presented.)",

keywords = "Amino acids, Carbohydrates, Glycopeptides, Glycosides, Glycosylations, Peptides",

author = "Horst Kessler and Katja Michael and Matthias Kottenhahn",

year = "1994",

doi = "10.1002/jlac.199419940809",

language = "English",

volume = "1994",

pages = "811--816",

journal = "Liebigs Annalen der Chemie",

issn = "0170-2041",

publisher = "VCH Verlagsgesellschaft",

number = "8",

}

TY - JOUR

T1 - TMS Triflate‐Promoted O‐Glycosylation of Amino Acids and Peptides by L‐Acosaminal and L‐Ristosaminal

AU - Kessler, Horst

AU - Michael, Katja

AU - Kottenhahn, Matthias

PY - 1994

Y1 - 1994

N2 - Cyclic and linear peptides are stereoselectively O‐glycosylated by 3‐(acylamino)glycals through activation with TMS triflate (trimethylsilyl trifluoromethanesulfonate) without Ferrier rearrangement. The yields of the 2‐deoxy‐α‐O‐glycosides obtained range from 18 to 95%. (Formula Presented.)

AB - Cyclic and linear peptides are stereoselectively O‐glycosylated by 3‐(acylamino)glycals through activation with TMS triflate (trimethylsilyl trifluoromethanesulfonate) without Ferrier rearrangement. The yields of the 2‐deoxy‐α‐O‐glycosides obtained range from 18 to 95%. (Formula Presented.)

KW - Amino acids

KW - Carbohydrates

KW - Glycopeptides

KW - Glycosides

KW - Glycosylations

KW - Peptides

UR - https://www.scopus.com/pages/publications/84988106766

U2 - 10.1002/jlac.199419940809

DO - 10.1002/jlac.199419940809

M3 - Article

AN - SCOPUS:84988106766

SN - 0170-2041

VL - 1994

SP - 811

EP - 816

JO - Liebigs Annalen der Chemie

JF - Liebigs Annalen der Chemie

IS - 8

ER -

TMS Triflate‐Promoted O‐Glycosylation of Amino Acids and Peptides by L‐Acosaminal and L‐Ristosaminal

Abstract

Keywords

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