Abstract
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.
Highlights
Introduction αAmino acids, one of the important classes of natural products, play fundamental roles in chemistry and biology
Α-aminoadipic acid has received attention from chemists active in the areas of peptide chemistry, organic synthesis, biosynthesis, and neuroscience. (R)-α-Aminoadipic acid exhibits a selective antagonistic activity at the N-methyl-D-aspartate subtype of glutamate receptors [6, 7]. It has been used in the synthesis of carbocyclic nucleoside precursors [8]. (R)-α-Aminoadipic acid 1 is a constituent of cephalosporin C and penicillin
Known as homoproline or piperidine2-carboxylic acid, a six-carbon natural nonproteinogenic α-amino acid, is an intermediate of lysine metabolism in various organisms including bacteria, yeast, fungi, and mammals. (S)-Pipecolic acid is an important precursor of several bioactive compounds such as synthetic peptides [12], local anesthetics [13], and potential enzyme inhibitors [14, 15] and is a component of biologically important natural products such as the immunomodulators rapamycin [16], the immunosuppressant FK506 [17], the antitumor antibiotic sandramycin [18], and the anticancer agent VX710 [19]
Summary
Introduction α-Amino acids, one of the important classes of natural products, play fundamental roles in chemistry and biology In addition to their vital roles as building block of proteins and as intermediates in metabolism, they constitute a broad array of chiral pool building blocks and organocatalysts [1,2,3]. (S)-Pipecolic acid is an important precursor of several bioactive compounds such as synthetic peptides [12], local anesthetics [13], and potential enzyme inhibitors [14, 15] and is a component of biologically important natural products such as the immunomodulators rapamycin [16], the immunosuppressant FK506 [17], the antitumor antibiotic sandramycin [18], and the anticancer agent VX710 [19] It occurs in the efrapeptins and neoefrapeptins, ATPase inhibiting peptide families [20].
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