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(R)-α-Aminoadipic Acid: A Versatile Precursor for the Synthesis of D-Amino Acids

The ready accessibility of (R)-α-aminoadipic acid by enzymatic cleavage of cephalosporin C (CephC) in the production of 7-aminocephalosporanic acid (7-ACA) on a large scale makes it a favorable chiral pool building block for the synthesis of unusual amino acids. A route for the synthesis of C-5-alke...

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Detalles Bibliográficos
Autores principales: Sadiq, Amina, Sewald, Norbert
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Hindawi Publishing Corporation 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3810487/
https://www.ncbi.nlm.nih.gov/pubmed/24222844
http://dx.doi.org/10.1155/2013/252813
Descripción
Sumario:The ready accessibility of (R)-α-aminoadipic acid by enzymatic cleavage of cephalosporin C (CephC) in the production of 7-aminocephalosporanic acid (7-ACA) on a large scale makes it a favorable chiral pool building block for the synthesis of unusual amino acids. A route for the synthesis of C-5-alkenyl and C-6-alkylidene derivatives of (R)-pipecolic acid is described which utilizes (R)-α-aminoadipic acid as the enantiomerically pure starting material. Moreover, the synthesis of azido and triazolyl derivatives of (R)-α-aminoadipic acid is reported.