Fakultät für Chemie - Former
 
 
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Bielefeld University > Department of Chemistry > Organic Chemistry III > Team > Former

Personal data for Dr. Amina Sadiq

  Dr. Amina Sadiq
Dr. Amina Sadiq
Raum: F2-231
Telefon: 0521 106 2152
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(R)-alpha-Aminoadipic acid: an interesting chiral pool building block for amino acid and peptide chemistry


Amino acids are appreciated by synthetic chemists as inexpensive and versatile enantiomerically pure building blocks. Besides in the synthesis of peptides and peptidomimetics, amino acids found widespread application as starting materials or even catalysts in the synthesis of a broad range of compounds.[1](R)-Configured amino acids do not occur in Nature as frequently as their (S)-configured enantiomers. (R)-Amino acids exert conformational bias, when they are incorporated e.g. in cyclic peptides.[2] Moreover, the sense of chirality also renders them interesting starting materials for synthesis.

(R)-α-Aminoadipic acid 1 is a constituent of penicillin N and cephalosporin C. In the semisynthesis of other penicillin and cephalosporin derivatives (R)-α-aminoadipic acid is first cleaved by chemical or enzymatic means to give 6-aminopenicillanic acid (6-APA) and 7-aminocephalosporanic acid (7-ACA), resp. 6-APA and 7-ACA are then acylated to give different penicillins and cephalosporins. In the case of cephalosporin C cleavage by cephalosporin acylase provides (R)-α-aminoadipic acid as a side product in large quantities.[3]



We therefore embarked on a project to explore, how the enantiomerically pure (R)-α-aminoadipic acid could be used as a building block in the preparation of other compounds. Besides the known conversion into the δ-lactam 2, we envisaged the transformation into benzyl 1-benzyloxycarbonyl-5-formyl-1,2,3,4-tetrahydropyridine-2-carboxylate 3 and (R)-pipecolic acid 4.[4]


References


[1] Hughes, A. B. (Ed.), Amino Acids, Peptides and Proteins in Organic Chemistry, Wiley-VCH: Weinheim 2009.

[2] Royo Gracia, S., Gaus, K., Sewald, N., Future Med. Chem.2009, 1, 1289-1310.

[3] Sonawane, V. C., Crit. Rev. Biotechnol.2006, 26, 95-120.

[4] Sadiq, A., Sewald, N., Arkivoc2012, v, 28-36.