15785-52-1

Basic information

• Product Name: Cyclopropylalanine
• Synonyms: Cyclopropylalanine;(+/-)-alpha-Aminocyclopropanepropanoic acid;3-Cyclopropylalanine;alhpa-Aminocyclopropanepropanoic acid;Cyclopropanealanine;DL-alpha-Aminocyclopropanepropionic acid;2-aMino-3-cyclopropylpropanoic acid;DL-3-cyclopropylalanine
• CAS NO: 15785-52-1
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.157
• Mol File: 15785-52-1.mol

Chemical Properties

• Boiling Point: 258℃
• Flash Point: 110℃
• Appearance: /
• Density: 1.218
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 2.32±0.10(Predicted)
• CAS DataBase Reference: Cyclopropylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropylalanine(15785-52-1)
• EPA Substance Registry System: Cyclopropylalanine(15785-52-1)

Safety Data

• Hazardous Substances Data: 15785-52-1(Hazardous Substances Data)

Usage

Uses

Used in Scientific Research:
Cyclopropylalanine is used as a research tool for studying the effects of amino acid modifications on protein function and structure. It allows researchers to investigate the role of specific amino acids in protein interactions and stability.
Used in Pharmaceutical Development:
Cyclopropylalanine is used as a building block in the development of new pharmaceutical drugs. Its ability to alter the biological activity of peptides makes it a valuable component in the design of novel therapeutic agents.
Used in Enzyme and Protein Targeting:
Cyclopropylalanine is used as a specific inhibitor or modulator for certain enzymes and proteins. By incorporating it into peptides, researchers can study the effects on enzyme activity and protein function, potentially leading to the development of targeted therapies for various diseases.
Used in Peptide Synthesis:
Cyclopropylalanine is used as a non-natural amino acid in the synthesis of modified peptides. This allows for the creation of peptides with altered properties, which can be used in research or as potential therapeutic agents.

InChI:InChI=1S/C6H11NO2/c7-5(6(8)9)3-4-1-2-4/h4-5H,1-3,7H2,(H,8,9)

Upstream product

• 18941-95-2 cyclopropylmethyl-formylamino-malonic acid diethyl ester 
• 33574-02-6 cyclopropylmethyl iodide 
• 170115-96-5 2-amino-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylacetamide 
• 133992-69-5 N-acetyl-3-cyclopropylalanine 
• 1198409-01-6 (1S)-1-methyl-2-oxo-2-tetrahydro-1H-pyrrolylethyl N-(p-methoxyphenyl)-2-amino-3-cyclopropylpropanoate 
• 1198408-99-9 (1S)-1-methyl-2-oxo-2-tetrahydro-1H-pyrrolylethyl 2-bromo-3-cyclopropylpropanoate 
• 174543-84-1 diethyl cyclopropylacetamidomalonate 
• 1027976-19-7 cyclopropylacetamidomalonic acid 
• 200482-55-9 4-cyclopropylmethylene-2-phenyl-4H-oxazol-5-one 
• 406681-37-6 (2S)-2-tert-butoxycarbonylamino-3-cyclopropyl-propionic acid benzyl ester 
• 849340-24-5 2-tert-butoxycarbonylamino-3-cyclopropylacrylic acid benzyl ester 
• 113741-17-6 (S)-2-amino-3-cyclopropylpropionic acid benzyl ester 
• 102693-69-6 (S)-2-Benzyloxycarbonylamino-3-cyclopropyl-propionic acid benzyl ester 
• 170642-22-5 (R)-2-Amino-3-cyclopropyl-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-propionamide 

Downstream Products

• 89483-08-9 (R)-2-((tert-butoxycarbonyl)amino)-3-cyclopropylpropanoic acid 
• 206438-31-5 methyl (S)-2-amino-3-cyclopropylpropanoate hydrochloride 
• 1038393-52-0 (S)-2-amino-3-cyclopropylpropan-1-ol 

Relevant articles and documents

METHOD OF PRODUCING OPTICALLY ACTIVE AMINO ACID DERIVATIVE

The present application relates to a method for producing an optically active α-amino acid derivative, comprising steps of reacting an α-haloester derivative represented by the general formula (1): of which alcohol part of the ester group is an optically active alcohol derivative, with an amine compound; then deprotecting the obtained compound; further carrying out an ester exchange reaction. According to the present invention method, it is possible to easily produce an optically active α-amino acid ester derivative which is useful as an intermediate for drugs with high selectivity.

The preparation of enantiomerically pure cyclopropylalanine

Single enantiomer cyclopropylalanine (>99.9% ee) and various derivatives were prepared using an asymmetric hydrogenation approach with a rhodium catalyst based on the methyl BoPhoz ligand. N-Boc cyclopropylalanine benzyl ester was the preferred derivative

Phosphinoferrocenylaminophosphines as novel and practical ligands for asymmetric catalysis

(Matrix Presented) A new series of ligands with a novel phosphine-aminophosphine ligation design as depicted in structure 1 has been prepared on a ferrocenylethyl backbone. These BoPhoz ligands of structure 2 have afforded exceedingly high activity and enantioselectivity in the rhodium-catalyzed asymmetric hydrogenation of dehydro-α-amino acid derivatives, itaconic acids, and α-ketoesters. These air-stable ligands are readily prepared from cost-effective and non-pyrophoric intermediates.

Highly practical methodology for the synthesis of D- and L-α-amino acids, N-protected α-amino acids, and N-methyl-α-amino acids

Full details are provided for an exceedingly practical method to synthesize D- and L-α-amino acids, N-protected α-amino acids, and N-methyl-α-amino acids, employing as a key step the asymmetric alkylation of pseudoephedrine glycinamide (1) or pseudoephedrine sarcosinamide (2). Practical procedures for the synthesis of 1 and 2 from pseudoephedrine and glycine methyl ester or sarcosine methyl ester, respectively, are presented. Optimum protocols for the enolization and subsequent alkylation of 1 and 2 are described. Alkylation reactions of 1 and 2 are found to be quite efficient with a wide range of alkyl halide substrates, and the products are formed with high diastereoselectivity. The products of these alkylation reactions are hydrolyzed efficiently and with little to no racemization simply by heating in water or water-dioxane mixtures. This protocol provides an exceedingly practical method for the preparation of salt-free α-amino acids of high enantiomeric purity. Alternatively, the alkylation products may be hydrolyzed in high yield and with little to no racemization by heating with aqueous sodium hydroxide. The alkaline hydrolyzate can then be treated with an acylating reagent to provide directly highly enantiomerically enriched N-protected derivatives such as N-Boc and N-Fmoc. Key features necessary for the successful execution of these experimental procedures are identified.

Kinetic Resolution of Unnatural and Rarely Occuring Amino Acids: Enantioselective Hydrolysis of N-Acyl Amino Acids Catalyzed by Acylase I

Acylase I (aminoacylase; N-acylamino-acid amidohydrolase, EC 3.5.1.14, from porcine kidney and the fungus Aspergillus) is broadly applicable enzymatic catalyst for the kinetic resolution of unnatural and rarely occuring α-amino acids.Its enantioselectivity for the hydrolysis of N-acyl L-α-amino acids is nearly absolute, yet it accepts substrates having a wide range of structure and functionality.This paper reports the initial rates of enzyme-catalyzed hydrolysis of over 50 N-acyl amino acids and analogues, the stabilities of the enzymes in aqueous and aqueous/organic solutions, and the effects of different acyl groups and metal ions on the rates of enzymatic hydrolysis.Eleven α-amino and α-methyl α-amino acids were resolved on a 2-29-g scale.Crude L- and D-amino acid products had generally >90percent ee.The utility of resolved amino acids as chiral synthons was illustrated by the preparation of (R)- and (S)-1-butene oxide and the diastereoselective (cis:trans, 7-8:1) iodolactonization of three 2-amino-4-alkenoic acid derivatives.

CYCLOPROPYLALANINE, AN ANTIFUNGAL AMINO ACID OF THE MUSHROOM AMANITA VIRGINEOIDES BAS

Cyclopropylalanine, an antifungal amino acid, has been isolated from the mushroom Amanita virgineoides Bas.Its structure has been elucidated as (2s)-2-amino-3-cyclopropylpropionic acid, on the basis of the spectroscopic analysis and its synthesis from L-allylglycine.