121786-39-8

Basic information

• Product Name: D-CYCLOPROPYLALANINE
• Synonyms: 3-CYCLOPROPYL-D-ALANINE;BETA-CYCLOPROPYL-D-ALANINE;D-CYCLOPROPYLALANINE;H-BETA-CYCLOPROPYL-D-ALA-OH;H-D-ALA(BETA-CYCLOPROPYL)-OH;H-D-ALA(CPRO)-OH;H-D-ALA(CYCLOPROPYL)-OH;(R)-2-AMINO-3-CYCLOPROPYL-PROPIONIC ACID
• CAS NO: 121786-39-8
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.16
• Product Categories: Amino Acids;Unusual amino acids;pharmacetical;a-amino;Pyridines
• Mol File: 121786-39-8.mol

Chemical Properties

• Boiling Point: 258.041 °C at 760 mmHg
• Flash Point: 109.86 °C
• Appearance: /
• Density: 1.218 g/cm³
• Vapor Pressure: 0.00994mmHg at 25°C
• Refractive Index: 1.496
• Storage Temp.: -15°C
• PKA: 2.32±0.10(Predicted)
• CAS DataBase Reference: D-CYCLOPROPYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: D-CYCLOPROPYLALANINE(121786-39-8)
• EPA Substance Registry System: D-CYCLOPROPYLALANINE(121786-39-8)

Safety Data

• Hazardous Substances Data: 121786-39-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
D-Cyclopropylalanine is used as a building block in the synthesis of heterocyclo-fused [1,3]oxazepines and -thiazepines and their analogs. These compounds serve as inhibitors of neutral endopeptidase and angiotensin-converting enzyme, which are important targets for the development of drugs to treat hypertension and other cardiovascular diseases.
Used in Chemical Synthesis:
D-Cyclopropylalanine is used as a key intermediate in the synthesis of various heterocyclic compounds with potential applications in medicinal chemistry and drug discovery. Its unique cyclopropane-containing side chain allows for the formation of novel ring systems and the exploration of new chemical space for the development of bioactive molecules.

InChI:InChI=1/C6H11NO2/c1-4(6(8)9)7-5-2-3-5/h4-5,7H,2-3H2,1H3,(H,8,9)/t4-/m1/s1

Upstream product

• 133992-69-5 N-acetyl-3-cyclopropylalanine 
• 33574-02-6 cyclopropylmethyl iodide 
• 170115-96-5 2-amino-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylacetamide 
• 170642-22-5 (R)-2-Amino-3-cyclopropyl-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-propionamide 
• 1198408-99-9 (1S)-1-methyl-2-oxo-2-tetrahydro-1H-pyrrolylethyl 2-bromo-3-cyclopropylpropanoate 
• 1198409-01-6 (1S)-1-methyl-2-oxo-2-tetrahydro-1H-pyrrolylethyl N-(p-methoxyphenyl)-2-amino-3-cyclopropylpropanoate 

Downstream Products

• 89483-08-9 (R)-2-((tert-butoxycarbonyl)amino)-3-cyclopropylpropanoic acid 

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.

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.