49606-99-7

Basic information

• Product Name: L-Cyclopropylglycine
• Synonyms: L-CYCLOPROPYLGLYCINE;2-CYCLOPROPYL-L-GLYCINE;(S)-AMINO-CYCLOPROPYL-ACETIC ACID;L-CYCLOPROPYLGLYCINE 98%;(S)-Amino-cyclopropyl-acetic acid hydrochloride;(S)-2-aMino-2-cyclopropylacetic acid;L-alpha-Cyclopropylglycine;(S)-2-Cyclopropylglycine
• CAS NO: 49606-99-7
• Molecular Formula: C₅H₉NO₂
• Molecular Weight: 115.13
• EINECS: 1312995-182-4
• Product Categories: Amino Acids;Unusual amino acids;pharmacetical;Amino Acid Derivatives;API;Amino Acids;a-amino
• Mol File: 49606-99-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 253.5 °C at 760 mmHg
• Flash Point: 107.1 °C
• Appearance: White to off-white/Crystalline
• Density: 1.2 g/cm³
• Vapor Pressure: 0.00567mmHg at 25°C
• Refractive Index: 1.559
• Storage Temp.: 2-8°C
• PKA: 2.40±0.10(Predicted)
• Water Solubility: Soluble in water. Insoluble in ethanol.
• BRN: 5728866
• CAS DataBase Reference: L-Cyclopropylglycine(CAS DataBase Reference)
• NIST Chemistry Reference: L-Cyclopropylglycine(49606-99-7)
• EPA Substance Registry System: L-Cyclopropylglycine(49606-99-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 49606-99-7(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

Uses

2-Cyclopropyl-L-glycine is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

InChI:InChI=1/C5H9NO2/c6-4(5(7)8)3-1-2-3/h3-4H,1-2,6H2,(H,7,8)/t4-/m0/s1

Upstream product

• 13885-13-7 2-cyclopropyl-2-oxoacetic acid 
• 56512-18-6 2-cyclopropyl-2-oxo acetate potassium salt 
• 765-43-5 Cyclopropyl methyl ketone 
• 281191-43-3 (S)-2-cyclopropyl-2-((S)-1-phenylethylamino)acetic acid 
• 638207-64-4 methyl 2-(N-tert-butoxycarbonyl-N-chloroamino)-2-cyclopropylacetate 
• 638207-62-2 methyl 2-(N-tert-butoxycarbonylamino)-2-cyclopropylacetate 
• 768356-83-8 methyl 2-amino-2-cyclopropylacetate 
• 15785-26-9 (S)-2-amino-2-cyclopropyl acetic acid 
• 936097-37-9 cyclopropyl-hydroxyiminoacetic acid 
• 155976-13-9 (2S)-2-[[(tert-butoxy)carbonyl]amino]-2-cyclopropylacetic acid 
• 121703-92-2 N-Chloroacetyl-α-cyclopropylglycine 

Downstream Products

• 155976-13-9 (2S)-2-[[(tert-butoxy)carbonyl]amino]-2-cyclopropylacetic acid 
• 1173522-82-1 (S)-2-(1-cyclopropyl-2-methoxyethylamino)acetonitrile hydrochloride 
• 1360774-44-2 C₁₁H₂₁NO₃ 

Relevant articles and documents

Direct monitoring of biocatalytic deacetylation of amino acid substrates by1H NMR reveals fine details of substrate specificity

Amino acids are key synthetic building blocks that can be prepared in an enantiopure form by biocatalytic methods. We show that thel-selective ornithine deacetylase ArgE catalyses hydrolysis of a wide-range ofN-acyl-amino acid substrates. This activity was revealed by1H NMR spectroscopy that monitored the appearance of the well resolved signal of the acetate product. Furthermore, the assay was used to probe the subtle structural selectivity of the biocatalyst using a substrate that could adopt different rotameric conformations.

SYNTHESIS METHOD FOR L-CYCLIC ALKYL AMINO ACID AND PHARMACEUTICAL COMPOSITION HAVING THEREOF

A synthesis method for L-cyclic alkyl amino acid and a pharmaceutical composition having the said amino acid are provide in the present disclosure provides. The synthesis method comprises: step A.) preparing a cyclic alkyl keto acid or a cyclic alkyl keto acid salt having Structural Formula (I) or Structural Formula (II), and step B.) mixing the cyclic alkyl keto acid or the cyclic alkyl keto acid salt with ammonium formate, a leucine dehydrogenase, a formate dehydrogenase and a coenzyme NAD+, and carrying out a reductive amination reaction to generate the L-cyclic alkyl amino acid, wherein the Structural Formula (I) is where n1≧1, m1≧0 and the M1 is H or a monovalent cation; the Structural Formula (II) is where n2≧0, m2≧0, the M2 is H or a monovalent cation, an amino acid sequence of the leucine dehydrogenase is SEQ ID No.1.

Practical syntheses of both enantiomers of cyclopropylglycine and of methyl 2-cyclopropyl-2-N-Boc-iminoacetate

A facile three-step synthesis of racemic cyclopropylglycine in multigram quantities from inexpensive cyclopropyl methyl ketone has been elaborated. Enzymatic hydrolysis of the N-Boc-protected methyl ester of cyclopropylglycine 9 with the inexpensive enzyme papain from Carica papaya affords both enantiomers of cyclopropylglycine (8) with enantiomeric excesses of 99% or better after deprotection under acidic conditions. Furthermore, the new cyclopropyl group-containing building block methyl 2-cyclopropyl-2-N-Boc-iminoacetate (13) was prepared by N-chlorination and subsequent dehydrochlorination with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Addition of nucleophiles to 13 offers a ready access to an unusual, orthogonally bisprotected α,α-diamino acid derivative and interesting components of rigid peptide backbones.