136120-77-9

Upstream product

• 56-89-3 L-cystine 
• 58635-29-3 N-(4-methoxybenzyloxycarbonyl)-α-(4-methoxybenzylester)-δ-L-α-aminoadipic acid 

Downstream Products

• 136120-78-0 N-4-methoxybenzyloxycarbonyl-α-4-methoxybenzylester-δ-(L-α-aminoadipoyl)-L-cystinyl-D-cyanoalanine benzhydrylester 

Relevant academic research and scientific papers

Formation of Novel Unsaturated Side Chain Penicillins with Isopenicillin N Synthase

Incubation of δ-L-α-aminoadipoyl-L-cysteinyl-D-propargylglycine (3) and δ-L-α-aminoadipoyl-L-cysteinyl-D-cyanoalanine (4) with isopenicillin N synthase resulted in the formation of three novel penicillin antibiotics, possessing unsaturated side chain (10), (11), and (12).

NEW PENICILLINS FROM ISOPENICILLIN N SYNTHASE.

The three tripeptides δ-L-α-aminoadipoyl-L-cysteinyl-D-propargylglycine, δ-L-α-aminoadipoyl-L-cysteinyl-D-cyanoalanine and δ-L-α-aminoadipoyl-L-cysteinyl-D--norvaline were synthesised and incubated with the enzyme Isopenicillin N Synthase (IPNS).All incubation mixtures contained biologically active products, and led to the isolation of four new penicillins (β-ethyl, α-acetylenic, α- and β-nitrile) following purification by reverse phase HPLC.The stereochemistries of formation of monosubstituted penicillins with IPNS are rationalised.