23458-22-2

Upstream product

• 49760-60-3 N-benzyloxycarbonyl-L-alanyl chloride 
• 16652-71-4 benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride 
• 5513-39-3 N-benzyloxycarbonyl-alanine benzyl ester 
• 130446-89-8 Z-L-Ala 2-chloroethyl ester 
• 88718-12-1 Z-L-Ala benzyl ester 
• 28819-05-8 (S)-2-benzyloxycarbonylamino-propionic acid methyl ester 
• 41324-66-7 H-Pro-OBzl 
• 1142-20-7 N-Cbz-Ala 

Downstream Products

• 3918-95-4 alanylproline 

Relevant academic research and scientific papers

Incorporation of unnatural amino acid derivatives into a peptide bond via an oxime ester catalysed by papain or lipase

In the presence of an oxime in the reaction solution, papain and lipase P (Pseudomonas from Amano) catalysed the stereoselective transesterification of an N-protected amino acid or peptide ester to form an active (oxime) ester which in turn underwent peptide bond formation with several natural and unnatural amino acid derivatives (proline, N-methylglycine, N-methylalanine, α-methylphenylalanine).

Chemo-enzymatic synthesis of optically active amino acids and peptides

The industrial alkaline protease, alcalase, is stable and active in a high concentration of organic solvents and useful as a biocatalyst for (i) diastereoselective hydrolysis of peptide esters and preparation of racemization-free peptides; (ii) selective incorporation of esters of D-amino acid into peptides in t-butanol via a selective hydrolysis of esters of D,L-amino acid, followed by using the unhydrolyzed D-esters as a nucleophile in a kinetically controlled peptide bond formation; (iii) resolution of esters of amino acid in 95% t-butanol/5% water, followed by saponification of the unreacted esters to offer both enantiomers with high yield and optical purity; (iv) completely resolve amino-acid esters with high yield and optical purity via in situ racemization of the unreacted antipode catalyzed by pyridoxal 5-phosphate; (v) cryobioorganic synthesis of peptides with increased yields 15%-40% of peptide bond formation by reaction at 5 °C instead of 25-30 °C of a kinetically controlled enzymatic reaction in alcohols.

Amino Acids and Peptides; 67. Easy Preparation and Use of Benzyloxycarbonyl Derivatives of Amino Acid Chlorides and α-Hydroxycarboxylic Acid Chlorides

N-Benzyloxycarbonyl amino acid chlorides and α-benzyloxycarbonyloxy carboxylic acid chlorides are readily available by treating the corresponding carboxylic acids with 1-chloro-N,N,2-trimethyl-1-propen-1-amine.They can be immediately reacted with O-, N- and C-nucleophiles to afford peptides, ketones and esters.