α-Azido acids for direct use in solid-phase peptide synthesis

Christian W. Torne; Peg Davis; Frank Porreca; Morten Meldal

doi:10.1002/1099-1387(200012)6:12<594::AID-PSC276>3.0.CO;2-X

α-Azido acids for direct use in solid-phase peptide synthesis

Christian W. Torne, Peg Davis, Frank Porreca, Morten Meldal

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

28 Scopus citations

Abstract

Several new α-azido acids have been synthesized and their use in solid-phase peptide synthesis has been demonstrated. The azido group allows for high activation of the carboxyl group as an acid chloride without formation of byproductions and with no detectable racemization. An analog of Leu-enkephalin has been prepared and tested in the mouse vas deferens and guinea pig ileum bioassays: it displays moderate activity as the δ-opiod receptor.

Original language	English (US)
Pages (from-to)	594-602
Number of pages	9
Journal	Journal of Peptide Science
Volume	6
Issue number	12
DOIs	https://doi.org/10.1002/1099-1387(200012)6:12<594::AID-PSC276>3.0.CO;2-X
State	Published - 2000

Keywords

Azido acid
Enkephalin
N-protection
SPPS

ASJC Scopus subject areas

Structural Biology
Biochemistry
Molecular Medicine
Molecular Biology
Pharmacology
Drug Discovery
Organic Chemistry

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10.1002/1099-1387(200012)6:12<594::AID-PSC276>3.0.CO;2-X

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abstract = "Several new α-azido acids have been synthesized and their use in solid-phase peptide synthesis has been demonstrated. The azido group allows for high activation of the carboxyl group as an acid chloride without formation of byproductions and with no detectable racemization. An analog of Leu-enkephalin has been prepared and tested in the mouse vas deferens and guinea pig ileum bioassays: it displays moderate activity as the δ-opiod receptor.",

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AU - Torne, Christian W.

AU - Davis, Peg

AU - Porreca, Frank

AU - Meldal, Morten

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Y1 - 2000

N2 - Several new α-azido acids have been synthesized and their use in solid-phase peptide synthesis has been demonstrated. The azido group allows for high activation of the carboxyl group as an acid chloride without formation of byproductions and with no detectable racemization. An analog of Leu-enkephalin has been prepared and tested in the mouse vas deferens and guinea pig ileum bioassays: it displays moderate activity as the δ-opiod receptor.

AB - Several new α-azido acids have been synthesized and their use in solid-phase peptide synthesis has been demonstrated. The azido group allows for high activation of the carboxyl group as an acid chloride without formation of byproductions and with no detectable racemization. An analog of Leu-enkephalin has been prepared and tested in the mouse vas deferens and guinea pig ileum bioassays: it displays moderate activity as the δ-opiod receptor.

KW - Azido acid

KW - Enkephalin

KW - N-protection

KW - SPPS

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ER -

α-Azido acids for direct use in solid-phase peptide synthesis

Abstract

Keywords

ASJC Scopus subject areas

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