28875-17-4Relevant articles and documents
Development of a temporary marker for peptides
Sameiro,Goncalves,Maia, Hernani L.S.
, p. 1480 - 1485 (2007/10/03)
3-[(N,N-Dimethylaminophenyl)-4′-diazenyl]benzoic acid was coupled with several amino acid esters and the product acylated further with Boc. The material thus obtained was then submitted to cleavage by electrolysis and nucleophilic attack in order to evaluate the possibility of using this chromophore as a temporary marker.
A temporary marker for biological applications
Sameiro, M,Gon?alves, T,Maia, Hernani L.S
, p. 7775 - 7777 (2007/10/03)
Having in mind the development of new colour labelled amino acid derivatives, a carboxyl azo dye was coupled to amino acid esters to give the corresponding orange N-acyl derivatives, which were in turn further acylated at their N-terminus with Boc for investigation of the conditions of possible cleavage of the chromophore by electrolysis or with nucleophiles. While difficulties were met with electrolysis owing to competitive reduction of the azo group, cleavage with N,N-diethylaminoethylamine (DEAEA) gave satisfactory results. This allows the use of the chromophore as a temporary marker.
Synthesis of a 3-aminopiperidin-2,5-dione as a conformationally constrained surrogate of the Ala-Gly dipeptide
Estiarte, M.Angels,Diez, Anna,Rubiralta, Mario,Jackson, Richard F.W
, p. 157 - 161 (2007/10/03)
The preparation of the Boc-{Ala-Gly}-OBn pseudopeptide 4 is reported. The key intermediate, aminoester 5b, was obtained by a cross-coupling reaction of alaninezinc iodide 6 and the thioester of glycine 9.
An efficient synthesis of [ring-14C]-L-tyrosine from [U-14C ]-phenol
Kendall, John T.
, p. 505 - 514 (2007/10/03)
The title compound was prepared in good overall yield and high enantiopurity via a five step route beginning with [U-14C]-phenol, 4. Benzyl ether 5 was prepared from 4 under standard conditions and underwent selective iodination at the 4-position in the presence of iodine and mercuric oxide. Palladium catalysed cross coupling of the resulting aryl iodide 6 and the organozinc intermediate derived from N-tert-butoxycarbonyl-3-iodo-alanine methyl ester, 7, proceeded smoothly to give 8. Debenzylation and acid hydrolysis afforded the deprotected amino acid as the hydrochloride salt. Purification (flash chromatography) was necessary in only two of the five steps in the synthesis.