50444-54-7

Basic information

• Product Name: Z-ALA-ALA-NH2
• Synonyms: Z-ALA-ALA-NH2;Cbz-Ala-Ala-NH2;Cbz-L-Ala-L-Ala-NH2;N-(Benzyloxycarbonyl)alanyl-L-alaninamide;Benzyl ((S)-1-(((S)-1-amino-1-oxopropan-2-yl)amino)-1-oxopropan-2-yl)carbamate
• CAS NO: 50444-54-7
• Molecular Formula: C₁₄H₁₉N₃O₄
• Molecular Weight: 293.32
• EINECS: 1533716-785-6
• Mol File: 50444-54-7.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 592.2°C at 760 mmHg
• Flash Point: 312°C
• Appearance: /Solid
• Density: 1.216g/cm³
• Vapor Pressure: 5.34E-14mmHg at 25°C
• Refractive Index: 1.543
• Storage Temp.: -15°C
• PKA: 11.14±0.46(Predicted)
• CAS DataBase Reference: Z-ALA-ALA-NH2(CAS DataBase Reference)
• NIST Chemistry Reference: Z-ALA-ALA-NH2(50444-54-7)
• EPA Substance Registry System: Z-ALA-ALA-NH2(50444-54-7)

Safety Data

• Hazardous Substances Data: 50444-54-7(Hazardous Substances Data)

Usage

Uses

Z-ALA-ALA-NH2 is used in preparation of substituted Iminothiazolidinone compounds as inhibitors of type III secretion in Gram-neg. bacteria useful in treatment of bacterial infection.

InChI:InChI=1/C14H19N3O4/c1-9(12(15)18)16-13(19)10(2)17-14(20)21-8-11-6-4-3-5-7-11/h3-7,9-10H,8H2,1-2H3,(H2,15,18)(H,16,19)(H,17,20)

Upstream product

• 7324-05-2 L-alanine amide 
• 67850-37-7 Z-L-Ala 2,2,2-trichloroethyl ester 
• 130446-89-8 Z-L-Ala 2-chloroethyl ester 
• 88718-12-1 Z-L-Ala benzyl ester 
• 1142-20-7 N-Cbz-Ala 
• 33208-99-0 (S)-alaninamide hydrochloride 
• 28819-05-8 (S)-2-benzyloxycarbonylamino-propionic acid methyl ester 
• 60625-90-3 Cbz-alanine ethyl ester 
• 4816-87-9 Z-L-Ala carbamoylmethyl ester 
• 13139-27-0 L-α-N-Cbz-alaninamide 
• 203640-41-9 Z-L-Ala 2,2,2-trifluoroethyl ester 

Relevant articles and documents

Mechanoenzymatic peptide and amide bond formation

Mechanochemical chemoenzymatic peptide and amide bond formation catalysed by papain was studied by ball milling. Despite the high-energy mixing experienced inside the ball mill, the biocatalyst proved stable and highly efficient to catalyse the formation of α,α- and α,β-dipeptides. This strategy was further extended to the enzymatic acylation of amines by milling, and to the mechanosynthesis of a derivative of the valuable dipeptide L-alanyl-l-glutamine.

Enzymatic C-terminal amidation of amino acids and peptides

Herein, we describe two versatile and high yielding enzymatic approaches for the conversion of semi-protected amino acid and peptidyl C-terminal α-carboxylic acids into their corresponding amides. In the first approach, the lipase Candida antarctica lipase-B (Cal-B), and in the second approach, the protease Subtilisin A, are used, respectively. We found that by using the ammonium salt of the α-carboxylic acid instead of separate ammonia sources, the enzymatic amidation reactions proceeded much faster without side reactions and gave near to quantitative yields of products.

α-Chymotrypsin-catalyzed peptide synthesis in frozen aqueous solution using N-protected amino acid carbamoylmethyl esters as acyl donors

A kinetically controlled peptide synthesis catalyzed by α-chymotrypsin was performed in frozen aqueous solution (ice, -24 °C). The yield of the peptide was significantly improved by the use of the carbamoylmethyl (Cam) ester as the acyl donor instead of the conventional ethyl ester. The peptide yield increased up to ca. 90% when N-benzyloxycarbonyl (CBZ)-Phe-OCam and H-Phe-NH2 were used as the acyl donor and nucleophile, respectively. Such an improvement of the peptide yield in ice was also observed in the coupling of other CBZ-amino acid Cam esters as acyl donors. Furthermore, this approach was applied to the synthesis of peptides containing d-amino acids. The peptides such as CBZ-d-Phe-Phe-NH2, CBZ-Phe-d-Phe-NH2 and CBZ-d-Phe-d-Phe-NH2 were also obtained in excellent to moderate yields in ice. A high diastereoselectivity towards the l-l peptide was observed when the racemic amino acid Cam ester was used as the acyl donor in ice.