4-Amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic acid (β-TOAC), the first spin-labelled, cyclic, chiral β-amino acid resolved in an enantiomerically pure state

Karen Wright, Marco Crisma, Claudio Toniolo, Roland Török, A. Péter, Michel Wakselman, Jean Paul Mazaleyrat

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Amination of 3-carboxymethyl-1-oxyl-2,2,6,6-tetramethyl-4-piperidone with (R)-α-methylbenzylamine, NaBH3CN reduction of the resulting enamine and removal of the chiral auxiliary from the separated diastereoisomers, led to enantiomerically pure (3S,4S) and (3R,4R) methyl 4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylates.

Original languageEnglish
Pages (from-to)3381-3384
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number16
DOIs
Publication statusPublished - Apr 14 2003

Fingerprint

Cyclic Amino Acids
Amination
Carboxylic Acids
Amino Acids
tempidon
2,2,6,6-tetramethylpiperidine-N-oxide-4-amino-4-carboxylic acid
TEMPO

Keywords

  • Chiral nitroxides
  • Modified β-amino acids
  • Spin-labelled amino acids

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

4-Amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic acid (β-TOAC), the first spin-labelled, cyclic, chiral β-amino acid resolved in an enantiomerically pure state. / Wright, Karen; Crisma, Marco; Toniolo, Claudio; Török, Roland; Péter, A.; Wakselman, Michel; Mazaleyrat, Jean Paul.

In: Tetrahedron Letters, Vol. 44, No. 16, 14.04.2003, p. 3381-3384.

Research output: Contribution to journalArticle

Wright, Karen ; Crisma, Marco ; Toniolo, Claudio ; Török, Roland ; Péter, A. ; Wakselman, Michel ; Mazaleyrat, Jean Paul. / 4-Amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic acid (β-TOAC), the first spin-labelled, cyclic, chiral β-amino acid resolved in an enantiomerically pure state. In: Tetrahedron Letters. 2003 ; Vol. 44, No. 16. pp. 3381-3384.
@article{0df3fa072d69426aa283a3e583d14719,
title = "4-Amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic acid (β-TOAC), the first spin-labelled, cyclic, chiral β-amino acid resolved in an enantiomerically pure state",
abstract = "Amination of 3-carboxymethyl-1-oxyl-2,2,6,6-tetramethyl-4-piperidone with (R)-α-methylbenzylamine, NaBH3CN reduction of the resulting enamine and removal of the chiral auxiliary from the separated diastereoisomers, led to enantiomerically pure (3S,4S) and (3R,4R) methyl 4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylates.",
keywords = "Chiral nitroxides, Modified β-amino acids, Spin-labelled amino acids",
author = "Karen Wright and Marco Crisma and Claudio Toniolo and Roland T{\"o}r{\"o}k and A. P{\'e}ter and Michel Wakselman and Mazaleyrat, {Jean Paul}",
year = "2003",
month = "4",
day = "14",
doi = "10.1016/S0040-4039(03)00572-0",
language = "English",
volume = "44",
pages = "3381--3384",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "16",

}

TY - JOUR

T1 - 4-Amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic acid (β-TOAC), the first spin-labelled, cyclic, chiral β-amino acid resolved in an enantiomerically pure state

AU - Wright, Karen

AU - Crisma, Marco

AU - Toniolo, Claudio

AU - Török, Roland

AU - Péter, A.

AU - Wakselman, Michel

AU - Mazaleyrat, Jean Paul

PY - 2003/4/14

Y1 - 2003/4/14

N2 - Amination of 3-carboxymethyl-1-oxyl-2,2,6,6-tetramethyl-4-piperidone with (R)-α-methylbenzylamine, NaBH3CN reduction of the resulting enamine and removal of the chiral auxiliary from the separated diastereoisomers, led to enantiomerically pure (3S,4S) and (3R,4R) methyl 4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylates.

AB - Amination of 3-carboxymethyl-1-oxyl-2,2,6,6-tetramethyl-4-piperidone with (R)-α-methylbenzylamine, NaBH3CN reduction of the resulting enamine and removal of the chiral auxiliary from the separated diastereoisomers, led to enantiomerically pure (3S,4S) and (3R,4R) methyl 4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylates.

KW - Chiral nitroxides

KW - Modified β-amino acids

KW - Spin-labelled amino acids

UR - http://www.scopus.com/inward/record.url?scp=0037436914&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037436914&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(03)00572-0

DO - 10.1016/S0040-4039(03)00572-0

M3 - Article

VL - 44

SP - 3381

EP - 3384

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 16

ER -