27300-27-2Relevant articles and documents
Synthesis of 1-piperideine-6-carboxylic acid produced by L-lysine-ε-aminotransferase from the Streptomyces clavuligerus gene expressed in Escherichia coli
Wu, Mei-Li,Chen, Jun-Hao,Ho, Chi-Tang,Huang, Tzou-Chi
, p. 1767 - 1772 (2007)
The gene (laf) encoding L-lysine ε-aminotransferase (LAT) in Streptomyces clavuligerus was cloned and expressed in Escherichia coli. Nucleotide sequence analysis of lat predicted a single open reading frame (ORF) of 1371 bp, encoding a polypeptide of 457 amino acids with calculated molecular mass of 49.89 kDa. S. clavuligerus LAT was grouped into aminotransferase subfamily II of a family on the basis of sequence homology. A model system composed of the recombinant LAT in phosphate buffer was set up to study the biosynthesis of 2-acetyltetrahydropyridine. Lysine was found to be transformed to 1-piperideine-6-carboxylic acid. 2-Acetyltetrahydropyridine was characterized from the mixture of 1-piperideine-6-carboxylic acid and methylglyoxal. For the first time, we demonstrated that the L-lysine ε-aminotransferase is responsible for the formation of 1-piperideine-6-carboxylic acid, which may react with methylglyoxal to generate the acylated N-heterocyclic odorant 2-acetyltetrahydropyridine.
METHOD FOR SYNTHESISING 2-ACETYL-1-PYRROLINE AND THE STABLE PRECURSOR THEREOF, OPTIONALLY ISOTOPICALLY MARKED
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, (2012/05/04)
The present invention relates to a method for synthetizing a compound of the following formula (I): wherein R is a methyl or ethyl group, n is 1 or 2, and X is a CH2 or CD2 group, from a compound of the following formula (II): wherein R and n are as defined above, and also relates to a method for assaying the compounds of the formula (I) using a corresponding deuterated derivative as an internal reference, as well as to the use of ketal derivatives of compounds of the formula (I) as a stable precursor, in particular in a flavoring composition.
An efficient one-pot synthesis of pyrrolines and tetrahydropyridines from their chloro-precursors via in situ aza-Wittig reaction
Singh, Pradeep N.D.,Klima, Rodney F.,Muthukrishnan, Sivaramakrishnan,Murthy, Rajesh S.,Sankaranarayanan, Jagadis,Stahlecker, Heidi M.,Patel, Bhavika,Gudmundsdóttir, Anna D.
, p. 4213 - 4217 (2007/10/03)
A simple and efficient method for synthesizing pyrrolines and tetrahydropyridines via an intramolecular aza-Wittig reaction has been achieved by microwave irradiation of the corresponding chloro-alkane derivatives in the presence of tertiary phosphite and sodium azide. The in situ formation of the alkyl azides makes this a facile and safe method for aza-Wittig reactions.