Synthesis and resolution of new paramagnetic α-amino acids

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

New, paramagnetic unnatural α-amino acids were synthesized by the O'Donnell method. In the new amino acids nitroxide is condensed with thiophene, benzene, and tetrahydroisoquinoline ring, or linked through a methylene, benzyl or propargyl spacer. Some of the racemic paramagnetic α-amino acid esters described earlier or in this work were resolved by fractional crystallization of diastereomeric salts. Another approach for optically active paramagnetic amino acids is the modification of S-tyrosine derivatives with Pd-catalyzed cross-coupling reactions with paramagnetic acetylene and with a paramagnetic boronic acid.

Original languageEnglish
Pages (from-to)1094-1100
Number of pages7
JournalTetrahedron
Volume64
Issue number6
DOIs
Publication statusPublished - Feb 4 2008

Fingerprint

Amino Acids
Boronic Acids
Tetrahydroisoquinolines
Thiophenes
Acetylene
Cross Reactions
Crystallization
Benzene
Tyrosine
Esters
Salts
Derivatives

Keywords

  • Amino acid
  • Nitroxides
  • O'Donnell reaction
  • Pd-catalyzed cross-coupling
  • Resolution

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis and resolution of new paramagnetic α-amino acids. / Kalai, T.; Schindler, J.; Balog, Mária; Fogassy, E.; Hideg, K.

In: Tetrahedron, Vol. 64, No. 6, 04.02.2008, p. 1094-1100.

Research output: Contribution to journalArticle

@article{ad030a2d405e4773917b29a264dc7e27,
title = "Synthesis and resolution of new paramagnetic α-amino acids",
abstract = "New, paramagnetic unnatural α-amino acids were synthesized by the O'Donnell method. In the new amino acids nitroxide is condensed with thiophene, benzene, and tetrahydroisoquinoline ring, or linked through a methylene, benzyl or propargyl spacer. Some of the racemic paramagnetic α-amino acid esters described earlier or in this work were resolved by fractional crystallization of diastereomeric salts. Another approach for optically active paramagnetic amino acids is the modification of S-tyrosine derivatives with Pd-catalyzed cross-coupling reactions with paramagnetic acetylene and with a paramagnetic boronic acid.",
keywords = "Amino acid, Nitroxides, O'Donnell reaction, Pd-catalyzed cross-coupling, Resolution",
author = "T. Kalai and J. Schindler and M{\'a}ria Balog and E. Fogassy and K. Hideg",
year = "2008",
month = "2",
day = "4",
doi = "10.1016/j.tet.2007.11.020",
language = "English",
volume = "64",
pages = "1094--1100",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "6",

}

TY - JOUR

T1 - Synthesis and resolution of new paramagnetic α-amino acids

AU - Kalai, T.

AU - Schindler, J.

AU - Balog, Mária

AU - Fogassy, E.

AU - Hideg, K.

PY - 2008/2/4

Y1 - 2008/2/4

N2 - New, paramagnetic unnatural α-amino acids were synthesized by the O'Donnell method. In the new amino acids nitroxide is condensed with thiophene, benzene, and tetrahydroisoquinoline ring, or linked through a methylene, benzyl or propargyl spacer. Some of the racemic paramagnetic α-amino acid esters described earlier or in this work were resolved by fractional crystallization of diastereomeric salts. Another approach for optically active paramagnetic amino acids is the modification of S-tyrosine derivatives with Pd-catalyzed cross-coupling reactions with paramagnetic acetylene and with a paramagnetic boronic acid.

AB - New, paramagnetic unnatural α-amino acids were synthesized by the O'Donnell method. In the new amino acids nitroxide is condensed with thiophene, benzene, and tetrahydroisoquinoline ring, or linked through a methylene, benzyl or propargyl spacer. Some of the racemic paramagnetic α-amino acid esters described earlier or in this work were resolved by fractional crystallization of diastereomeric salts. Another approach for optically active paramagnetic amino acids is the modification of S-tyrosine derivatives with Pd-catalyzed cross-coupling reactions with paramagnetic acetylene and with a paramagnetic boronic acid.

KW - Amino acid

KW - Nitroxides

KW - O'Donnell reaction

KW - Pd-catalyzed cross-coupling

KW - Resolution

UR - http://www.scopus.com/inward/record.url?scp=37249032073&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37249032073&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2007.11.020

DO - 10.1016/j.tet.2007.11.020

M3 - Article

VL - 64

SP - 1094

EP - 1100

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 6

ER -