93133-50-7

Upstream product

• 72-18-4 L-valine 
• 52-90-4 L-Cysteine 
• 1118-90-7 L-homoglutamic acid 
• 77257-03-5 α-²H-(S)-valine 
• 79761-05-0 N-benzyloxycarbonyl-α-benzyl-δ-(L-α-aminoadipoyl)-S-benzyl-L-cysteinyl-D-valine benzyl ester 
• 87141-27-3 N-benzyloxycarbonyl-1-(p-nitrobenzyl)-δ-(L-α-aminoadipyl)-S-benzyl-L-cysteinyl-D-valine, benzhydryl ester 
• 24325-14-2 (2S)-2-[(phenylmethoxy)carbonyl]aminoadipic acid 
• 79761-10-7 [(N-benzyloxycarbonyl)-(α-benzyl)-δ-(L-α-aminoadipoyl)]-S-benzyl-L-cysteine 
• 79761-03-8 N-benzyloxycarbonyl-S-benzyl-L-cysteinyl-D-valine benzyl ester 
• 61852-70-8 D-valine, benzhydryl ester 
• 87141-25-1 N-benzyloxycarbonyl-1-(p-nitrobenzyl)-δ-(L-α-aminoadipyl)-S-benzyl-L-cysteine, benzhydryl ester 
• 87141-26-2 N-benzyloxycarbonyl-1-(p-nitrobenzyl)-δ-(L-α-aminoadipyl)-S-benzyl-L-cysteine 
• 87141-23-9 p-nitrobenzyl N-benzyloxycarbonyl-L-α-aminoadipate 
• 24325-17-5 N-benzyloxycarbonyl-α-benzylester-δ-L-α-aminoadipic acid 

Downstream Products

• 69644-78-6 bis[Aad(-Cys-D-Val)] 
• 525-94-0 isopenicillin N 
• 525-94-0 penicillin N 

Relevant academic research and scientific papers

Exchange of the valine 2-H in the biosynthesis of L-δ-(α-aminoadipoyl)-L-cysteinyl-D-valine

Incubation of [2-2H]-valine with purified ACV synthetase from both Cephalosporium acremonium and Streptomyces davuligerus produced L-δ-(α-aminoadipoyl)-L-cysteinyl-D-valine (ACV), determined by the essentially complete (>95%) loss of deuterium from the α position of the incorporated valine. Incubations with deuterium oxide/water as solvent produced ACV with significant incorporation of deuterium into the valinyl residue. These observations confirm the prior proposal that a single multifunctional enzyme is responsible for both the formation of the peptide bonds of ACV and the epimerisation of the valinyl residue.

Synthesis of δ-(L-α-Aminoadipyl)-L-cysteinyl-D-valine and δ-(L-α-Aminoadipyl)-L-cysteinyl-D-valylglycine

An efficient synthesis of δ-(L-α-aminoadipyl)-L-cysteinyl-D-valine (ACV; 1) and δ-(L-α-aminoadipyl)-L-cysteinyl-D-valylglycine (ACVG; 2) via the protected tripeptide N-benzyloxycarbonyl-1-(p-nitrobenzyl)-δ-(L-α-aminoadipyl)-S-benzyl-L-cysteinyl-D-valine,

Conversion of 17O/18O-Labelled &δ-(L-&α-Aminoadipyl)-L-cysteinyl-D-valine into 17O/18O-Labelled Isopenicillin N in a Cell-free Extract of C. acremonium

δ-(L-α-Amino17O/18O>-adipyl)-L-cysteinyl-D-valine was converted into isopenicillin N in cell-free extracts of Cephalosporium acremonium with no loss of 17O/18O label as shown by 17O n.m.r. spectroscopy and mass spectrometry; incubation of unlabelled tripeptide in a cell-free system containing 17O/18O-enriched water produced isopenicillin N with no incorporation of 17O/18O.

Synthesis of δ-(L-α-Aminoadipoyl)-L-cysteinyl-D-valine and some Carbon-13 and Nitrogen-15 Labelled Isotopomers

δ-(L-α-Aminoadipoyl)-L-cysteinyl-D-valine (7a), δ-(L-α-aminoadipoyl)-L-cysteinyl-D-valine (7b), δ-(L-α-aminoadipoyl)-L-cysteinyl-D-valine (7c), and δ-(L-α-aminoadipoyl)-L-cysteinyl-D-valine (7d) were prepared by conv