Pyrazines on solid support from peptides by periodinane oxidation of threonine side-chains. A quantitative chemical transformation (QCT) for combinatorial chemistry

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Standard

Pyrazines on solid support from peptides by periodinane oxidation of threonine side-chains. A quantitative chemical transformation (QCT) for combinatorial chemistry. / Christensen, Caspar; Tornøe, Christian W.; Meldal, Morten.

I: QSAR and Combinatorial Science, Bind 23, Nr. 2-3, 04.2004, s. 109-116.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Christensen, C, Tornøe, CW & Meldal, M 2004, 'Pyrazines on solid support from peptides by periodinane oxidation of threonine side-chains. A quantitative chemical transformation (QCT) for combinatorial chemistry', QSAR and Combinatorial Science, bind 23, nr. 2-3, s. 109-116. https://doi.org/10.1002/qsar.200320009

APA

Christensen, C., Tornøe, C. W., & Meldal, M. (2004). Pyrazines on solid support from peptides by periodinane oxidation of threonine side-chains. A quantitative chemical transformation (QCT) for combinatorial chemistry. QSAR and Combinatorial Science, 23(2-3), 109-116. https://doi.org/10.1002/qsar.200320009

Vancouver

Christensen C, Tornøe CW, Meldal M. Pyrazines on solid support from peptides by periodinane oxidation of threonine side-chains. A quantitative chemical transformation (QCT) for combinatorial chemistry. QSAR and Combinatorial Science. 2004 apr.;23(2-3):109-116. https://doi.org/10.1002/qsar.200320009

Author

Christensen, Caspar ; Tornøe, Christian W. ; Meldal, Morten. / Pyrazines on solid support from peptides by periodinane oxidation of threonine side-chains. A quantitative chemical transformation (QCT) for combinatorial chemistry. I: QSAR and Combinatorial Science. 2004 ; Bind 23, Nr. 2-3. s. 109-116.

Bibtex

@article{ac37d12710ee41b3861c8a8b1c92e029,
title = "Pyrazines on solid support from peptides by periodinane oxidation of threonine side-chains. A quantitative chemical transformation (QCT) for combinatorial chemistry",
abstract = "The β-hydroxymethylene in threonine residues adjacent to an N-terminal amino acid were subjected to oxidation effected by Dess-Martin periodinane on solid support. Fmoc-cleavage at the TV-terminal amino acid afforded 3,6-dihydro-III-pyrazin-2-one, which oxidized spontaneously to the 1H-pyrazin-2-ones (3a-v). A variety of naturally occurring and synthetic α-amino acids gave rise to a diverse subset of functionalized 1H-pyrazin-2-ones. An amino functionality in the side-chain of the N-terminal amino acid residue allowed elongation by conventional solid phase peptide chemistry (5a-b). Furthermore, elongation of the side-chain with Thr and a second amino acid followed by oxidation resulted in bis 1H-pyrazin-2-ones in high yield (8).",
keywords = "Dess Martin, Heterocycle on solid phase, PEGA resin, Peptide mimetic, Spontaneous cleavage-oxidation",
author = "Caspar Christensen and Torn{\o}e, {Christian W.} and Morten Meldal",
year = "2004",
month = apr,
doi = "10.1002/qsar.200320009",
language = "English",
volume = "23",
pages = "109--116",
journal = "Molecular Informatics",
issn = "1868-1743",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "2-3",

}

RIS

TY - JOUR

T1 - Pyrazines on solid support from peptides by periodinane oxidation of threonine side-chains. A quantitative chemical transformation (QCT) for combinatorial chemistry

AU - Christensen, Caspar

AU - Tornøe, Christian W.

AU - Meldal, Morten

PY - 2004/4

Y1 - 2004/4

N2 - The β-hydroxymethylene in threonine residues adjacent to an N-terminal amino acid were subjected to oxidation effected by Dess-Martin periodinane on solid support. Fmoc-cleavage at the TV-terminal amino acid afforded 3,6-dihydro-III-pyrazin-2-one, which oxidized spontaneously to the 1H-pyrazin-2-ones (3a-v). A variety of naturally occurring and synthetic α-amino acids gave rise to a diverse subset of functionalized 1H-pyrazin-2-ones. An amino functionality in the side-chain of the N-terminal amino acid residue allowed elongation by conventional solid phase peptide chemistry (5a-b). Furthermore, elongation of the side-chain with Thr and a second amino acid followed by oxidation resulted in bis 1H-pyrazin-2-ones in high yield (8).

AB - The β-hydroxymethylene in threonine residues adjacent to an N-terminal amino acid were subjected to oxidation effected by Dess-Martin periodinane on solid support. Fmoc-cleavage at the TV-terminal amino acid afforded 3,6-dihydro-III-pyrazin-2-one, which oxidized spontaneously to the 1H-pyrazin-2-ones (3a-v). A variety of naturally occurring and synthetic α-amino acids gave rise to a diverse subset of functionalized 1H-pyrazin-2-ones. An amino functionality in the side-chain of the N-terminal amino acid residue allowed elongation by conventional solid phase peptide chemistry (5a-b). Furthermore, elongation of the side-chain with Thr and a second amino acid followed by oxidation resulted in bis 1H-pyrazin-2-ones in high yield (8).

KW - Dess Martin

KW - Heterocycle on solid phase

KW - PEGA resin

KW - Peptide mimetic

KW - Spontaneous cleavage-oxidation

UR - http://www.scopus.com/inward/record.url?scp=8444251465&partnerID=8YFLogxK

U2 - 10.1002/qsar.200320009

DO - 10.1002/qsar.200320009

M3 - Journal article

AN - SCOPUS:8444251465

VL - 23

SP - 109

EP - 116

JO - Molecular Informatics

JF - Molecular Informatics

SN - 1868-1743

IS - 2-3

ER -

ID: 326847815