Molecules 2011-01-01

Simple and efficient synthesis of racemic 2-(tert-butoxycarbon-ylamino)-2-methyl-3-(1H-1,2,4-triazol-1-yl)propanoic acid, a new derivative of β-(1,2,4-triazol-1-yl)alanine.

Younas Aouine, Hassane Faraj, Anouar Alami, Abdelilah El-Hallaoui, Abdelrhani Elachqar, Abdelali Kerbal

Index: Molecules 16 , 3380-3390, (2011)

Full Text: HTML

Abstract

A simple synthetic approach to racemic N-tert-butyloxycarbonyl-2-methyl-3-(1H-1,2,4-triazol-1-yl)alanine (5) in four steps and 68% overall yield starting from oxazoline derivative 1 is reported. This synthesis involves the alkylation of 1H-1,2,4-triazole with an O-tosyloxazoline derivative, followed by an oxazoline ring-opening reaction and oxidation of the N-protected β‑aminoalcohol by potassium permanganate.

Related Compounds

  • 1H-1,2,4-Triazole...

Related Articles:

Incorporation of amino acid analogs during the biosynthesis of Escherichia coli aspartate transcarbamylase.

1980-09-09

[Biochim. Biophys. Acta 615(1) , 59-69, (1980)]

Synthesis of a novel histidine analogue and its efficient incorporation into a protein in vivo.

2003-09-01

[Protein Eng. 16 , 699-706, (2003)]

Classifying mutagens as to their specificity in causing the six possible transitions and transversions: a simple analysis using the Salmonella mutagenicity assay.

1986-01-01

[Environ. Mutagen. 8 , 9, (1986)]

Incorporation of an unnatural amino acid in the active site of porcine pancreatic phospholipase A2. Substitution of histidine by 1,2,4-triazole-3-alanine yields an enzyme with high activity at acidic pH.

1996-04-01

[Protein Eng. 9(4) , 345-52, (1996)]

Incorporation of 1,2,4-triazole-3-alanine into a mutant of phage lambda lysozyme containing a single histidine.

1998-03-01

[Protein Eng. 11(3) , 213-7, (1998)]

More Articles...