25613-60-9

Basic information

• Product Name: Z-L-Phenylalanine N-carboxyanhydride
• Synonyms: Z-Phe-Nca;Z-PHENYLALANINE NCA;CBZ-L-PHENYLALANINE N-CARBOXYANHYDRIDE;(S)-benzyl 4-benzyl-2,5-dioxooxazolidine-3-carboxylate;CBZ-Phe-NCA;Z-L-Phenylalanine N-carboxyanhydride
• CAS NO: 25613-60-9
• Molecular Formula: C₁₈H₁₅NO₅
• Molecular Weight: 325.319
• Mol File: 25613-60-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 108-109 °C
• Boiling Point: 451.3±38.0 °C(Predicted)
• Appearance: /
• Density: 1.353±0.06 g/cm3(Predicted)
• PKA: -3.09±0.40(Predicted)
• CAS DataBase Reference: Z-L-Phenylalanine N-carboxyanhydride(CAS DataBase Reference)
• NIST Chemistry Reference: Z-L-Phenylalanine N-carboxyanhydride(25613-60-9)
• EPA Substance Registry System: Z-L-Phenylalanine N-carboxyanhydride(25613-60-9)

Safety Data

• Hazardous Substances Data: 25613-60-9(Hazardous Substances Data)

Usage

General Description

Z-L-Phenylalanine N-carboxyanhydride is a chemical compound often used in the field of medicine and science, specifically in the creation of polypeptides and proteins. It possesses the ability to form peptide bonds, which are essential in creating large, complex proteins. The compound is also classified as a type of N-carboxyanhydride, which are used widely in polymer chemistry. This chemical is especially beneficial in the field of biochemistry and in laboratory experiments for its fast and efficient polymerization properties. It is crucial in the study and production of proteins and active biochemical agents.

Upstream product

• 64-17-5 ethanol 
• 25613-61-0 4-Benzyl-2,5-dioxo-oxazolidine-3-carboxylic acid benzyl ester 
• 501-53-1 benzyl chloroformate 
• 14825-82-2 L-phenylalanine-N-carboxyanhydride 

Downstream Products

• 158257-34-2 (S)-5-benzyl-1-benzyloxycarbonyl-4-hydroxy-2,5-dihydropyrrol-2-one 
• 157683-55-1 (3S)-3-[[(benzyloxy)carbonyl]amino]-2-oxo-4-phenylbutanoic acid methyl ester 
• 214122-05-1 (4S)-4-[[(benzyloxy)carbonyl]amino]-3-oxo-5-phenyl-2-triphenylphosphoranylidene-pentanenitrile 
• 158744-36-6 ethyl (S)-4-benzyloxycarbonylamino-3-oxo-5-phenylpentanoate 
• 14470-31-6 (S)-tert-butyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-methylbutanoate 
• 59830-60-3 benzyl (1S)-(1-formyl-2-phenylethyl)carbamate 

Relevant articles and documents

Practical syntheses of chiral α-amino acids and chiral half-esters by kinetic resolution of urethane-protected α-amino acid N-carboxyanhydrides and desymmetrization of cyclic meso-anhydrides with new modified cinchona alkaloid catalysts

The large-scale applications of the kinetic resolution of urethane-protected α-amino acid N-carboxyanhydrides (UNCAs) and the desymmetrization of cyclic meso-anhydrides using modified cinchona alkaloids are described. These asymmetric reactions are effective organocatalytic methods for the synthesis of chiral a-amino acids 6 and chiral half-esters 2 on an industrial scale, because the organocatalyst recovery and product purification can be carried out by a simple extractive procedure obviating a chromatographic purification step. The modified cinchona alkaloid catalysts (DHQD) 2AQN and (DHQ)2AQN, as reported by Deng and co-workers, are not readily available and therefore not suitable for industrial-scale synthesis. Various O-alkylated quinidine and quinine derivatives were prepared and screened as catalysts for the kinetic resolution of phenylalanine UNCA with alcohol. The readily prepared O-propargylquinidine (OPQD) and O-propargylquinine (OPQ) were discovered to be highly enantioselective and practical catalysts. These new catalysts were applied to the synthesis of chiral propargylglycine 24 and the key intermediate of BAY10-8888/PLD-118, 26, on an industrial scale, by the kinetic resolution of UNCA 22 and the desymmetrization of cyclic meso-anhydride 25, respectively.