Solid-phase glycosylation of peptide templates and on-bead MAS-NMR analysis: Perspectives for glycopeptide libraries

Charlotte Held Gotfredsen; Koen M. Halkes; Jens Øllgaard Duus; Morten Meldal; Les P. Miranda; Morten Grøtli

doi:10.1002/1521-3765(20010817)7:16<3584::AID-CHEM3584>3.0.CO;2-Z

Solid-phase glycosylation of peptide templates and on-bead MAS-NMR analysis: Perspectives for glycopeptide libraries

Charlotte Held Gotfredsen, Koen M. Halkes, Jens Øllgaard Duus, Morten Meldal, Les P. Miranda, Morten Grøtli

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

The efficient solid-phase glycosylation of amino acid side chains (serine (Ser), threonine (Thr), and tyrosine (Tyr)) in peptides was demonstrated with a variety of glycosyl trichloroacetimidate donors in high yields and purities. A novel photolabile linker, with no chiral centre, was introduced to facilitate analysis by both matrix-assisted laser desorption ionisation time of flight (MALDI-TOF) mass spectrometry and nanoprobe magic angle spinning (MAS) NMR spectroscopy. Product analysis by nanoprobe MAS NMR spectroscopy, LC-MS and MALDI-TOF mass spectrometry of the glycosylation reactions indicated that the reactivity order of the hydroxy side-chain functions of amino acids in peptides on the solid-phase was Tyr > Ser > Thr. The nearly quantitative glycosylation yields and the efficient on-bead product analysis by nanoprobe MAS NMR spectroscopy have made a truly solid-phase approach for the synthesis and analysis of glycopeptide libraries possible.

Original language	English
Journal	Chemistry: A European Journal
Volume	7
Issue number	16
Pages (from-to)	3584-3591
ISSN	0947-6539
DOIs	https://doi.org/10.1002/1521-3765(20010817)7:16<3584::AID-CHEM3584>3.0.CO;2-Z
Publication status	Published - 2001
Externally published	Yes

Keywords

Amino Acid Sequence
Carbohydrate Conformation
Glycopeptides
Glycosylation
Indicators and Reagents
Models, Molecular
Nuclear Magnetic Resonance, Biomolecular
Peptides
Protein Conformation
Serine
Threonine
Tyrosine
2ZD004190S Threonine
42HK56048U Tyrosine
452VLY9402 Serine
Ionization
Lasers
Mass spectrometry
Synthesis (chemical)
Amino acids
article
desorption
ionization
mass spectrometry
nuclear magnetic resonance
peptide synthesis
protein glycosylation
solid phase extraction
NMR spectroscopy
Photolabile linker
Solid-phase synthesis
T
X

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@article{448ff2c455ff497b9bb858f5f8231101,

title = "Solid-phase glycosylation of peptide templates and on-bead MAS-NMR analysis: Perspectives for glycopeptide libraries",

abstract = "The efficient solid-phase glycosylation of amino acid side chains (serine (Ser), threonine (Thr), and tyrosine (Tyr)) in peptides was demonstrated with a variety of glycosyl trichloroacetimidate donors in high yields and purities. A novel photolabile linker, with no chiral centre, was introduced to facilitate analysis by both matrix-assisted laser desorption ionisation time of flight (MALDI-TOF) mass spectrometry and nanoprobe magic angle spinning (MAS) NMR spectroscopy. Product analysis by nanoprobe MAS NMR spectroscopy, LC-MS and MALDI-TOF mass spectrometry of the glycosylation reactions indicated that the reactivity order of the hydroxy side-chain functions of amino acids in peptides on the solid-phase was Tyr > Ser > Thr. The nearly quantitative glycosylation yields and the efficient on-bead product analysis by nanoprobe MAS NMR spectroscopy have made a truly solid-phase approach for the synthesis and analysis of glycopeptide libraries possible.",

keywords = "Amino Acid Sequence, Carbohydrate Conformation, Glycopeptides, Glycosylation, Indicators and Reagents, Models, Molecular, Nuclear Magnetic Resonance, Biomolecular, Peptides, Protein Conformation, Serine, Threonine, Tyrosine, 2ZD004190S Threonine, 42HK56048U Tyrosine, 452VLY9402 Serine, Ionization, Lasers, Mass spectrometry, Synthesis (chemical), Amino acids, article, desorption, ionization, mass spectrometry, nuclear magnetic resonance, peptide synthesis, protein glycosylation, solid phase extraction, NMR spectroscopy, Photolabile linker, Solid-phase synthesis, T, X",

author = "Gotfredsen, {Charlotte Held} and Halkes, {Koen M.} and Duus, {Jens {\O}llgaard} and Morten Meldal and Miranda, {Les P.} and Morten Gr{\o}tli",

year = "2001",

doi = "10.1002/1521-3765(20010817)7:16<3584::AID-CHEM3584>3.0.CO;2-Z",

language = "English",

volume = "7",

pages = "3584--3591",

journal = "Chemistry: A European Journal",

issn = "0947-6539",

publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",

number = "16",

}

Solid-phase glycosylation of peptide templates and on-bead MAS-NMR analysis: Perspectives for glycopeptide libraries. / Gotfredsen, Charlotte Held; Halkes, Koen M.; Duus, Jens Øllgaard; Meldal, Morten; Miranda, Les P.; Grøtli, Morten.

In: Chemistry: A European Journal, Vol. 7, No. 16, 2001, p. 3584-3591.

Research output: Contribution to journal › Journal article › Research › peer-review

TY - JOUR

T1 - Solid-phase glycosylation of peptide templates and on-bead MAS-NMR analysis: Perspectives for glycopeptide libraries

AU - Gotfredsen, Charlotte Held

AU - Halkes, Koen M.

AU - Duus, Jens Øllgaard

AU - Meldal, Morten

AU - Miranda, Les P.

AU - Grøtli, Morten

PY - 2001

Y1 - 2001

N2 - The efficient solid-phase glycosylation of amino acid side chains (serine (Ser), threonine (Thr), and tyrosine (Tyr)) in peptides was demonstrated with a variety of glycosyl trichloroacetimidate donors in high yields and purities. A novel photolabile linker, with no chiral centre, was introduced to facilitate analysis by both matrix-assisted laser desorption ionisation time of flight (MALDI-TOF) mass spectrometry and nanoprobe magic angle spinning (MAS) NMR spectroscopy. Product analysis by nanoprobe MAS NMR spectroscopy, LC-MS and MALDI-TOF mass spectrometry of the glycosylation reactions indicated that the reactivity order of the hydroxy side-chain functions of amino acids in peptides on the solid-phase was Tyr > Ser > Thr. The nearly quantitative glycosylation yields and the efficient on-bead product analysis by nanoprobe MAS NMR spectroscopy have made a truly solid-phase approach for the synthesis and analysis of glycopeptide libraries possible.

AB - The efficient solid-phase glycosylation of amino acid side chains (serine (Ser), threonine (Thr), and tyrosine (Tyr)) in peptides was demonstrated with a variety of glycosyl trichloroacetimidate donors in high yields and purities. A novel photolabile linker, with no chiral centre, was introduced to facilitate analysis by both matrix-assisted laser desorption ionisation time of flight (MALDI-TOF) mass spectrometry and nanoprobe magic angle spinning (MAS) NMR spectroscopy. Product analysis by nanoprobe MAS NMR spectroscopy, LC-MS and MALDI-TOF mass spectrometry of the glycosylation reactions indicated that the reactivity order of the hydroxy side-chain functions of amino acids in peptides on the solid-phase was Tyr > Ser > Thr. The nearly quantitative glycosylation yields and the efficient on-bead product analysis by nanoprobe MAS NMR spectroscopy have made a truly solid-phase approach for the synthesis and analysis of glycopeptide libraries possible.

KW - Amino Acid Sequence

KW - Carbohydrate Conformation

KW - Glycopeptides

KW - Glycosylation

KW - Indicators and Reagents

KW - Models, Molecular

KW - Nuclear Magnetic Resonance, Biomolecular

KW - Peptides

KW - Protein Conformation

KW - Serine

KW - Threonine

KW - Tyrosine

KW - 2ZD004190S Threonine

KW - 42HK56048U Tyrosine

KW - 452VLY9402 Serine

KW - Ionization

KW - Lasers

KW - Mass spectrometry

KW - Synthesis (chemical)

KW - Amino acids

KW - article

KW - desorption

KW - ionization

KW - mass spectrometry

KW - nuclear magnetic resonance

KW - peptide synthesis

KW - protein glycosylation

KW - solid phase extraction

KW - NMR spectroscopy

KW - Photolabile linker

KW - Solid-phase synthesis

KW - T

KW - X

U2 - 10.1002/1521-3765(20010817)7:16<3584::AID-CHEM3584>3.0.CO;2-Z

DO - 10.1002/1521-3765(20010817)7:16<3584::AID-CHEM3584>3.0.CO;2-Z

M3 - Journal article

VL - 7

SP - 3584

EP - 3591

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

SN - 0947-6539

IS - 16

ER -