Cycloleucine Chemical Properties

Melting point:

320 °C (dec.) (lit.)

Boiling point:

239.22°C (rough estimate)

Density 

1.1426 (rough estimate)

refractive index 

1.4827 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO: < 1 mg/mL (ultrasonic) (insoluble or slightly soluble)

form 

Crystalline Flakes or Powder

pka

2.38±0.20(Predicted)

color 

White to beige

Water Solubility 

5 g/100 mL

Merck 

14,2734

BRN 

636626

CAS DataBase Reference

52-52-8(CAS DataBase Reference)

NIST Chemistry Reference

Cyclopentanecarboxylic acid, 1-amino-(52-52-8)

EPA Substance Registry System

Cyclopentanecarboxylic acid, 1-amino- (52-52-8)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22

Safety Statements 

22-24/25

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

GY2625000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29224999

Hazardous Substances Data

52-52-8(Hazardous Substances Data)

Toxicity

LD50 oral in rat: 290mg/kg

MSDS

• Language:English Provider:Cycloleucine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Cycloleucine Usage And Synthesis

Chemical Properties

WHITE TO BEIGE CRYSTALLINE FLAKES OR POWDER

Uses

NMDA receptor antagonist, inhibits nucleic acid methylation; adrenergic agonist

Uses

Cycloleucine can be used as a building block to synthesize:

• Phosphonylmethylaminocyclopentane-1-carboxylic acid by reacting with paraformaldehyde and diethylphosphite via Kabachnik-Field′s reaction.
• Benzo[b]thiophene-2-carboxylic acid {1-[1-(R)-(3-morpholin-4-ylpropylcarbamoyl)-2-phenylethylcarbamoyl]cyclopentyl}-amide, (MEN14268) as potential tachykinin NK2 receptor antagonist.

Uses

Cycloleucine is a synthetic amino acid used in numerous biochemical transport studies

Definition

ChEBI: A non-proteinogenic alpha-amino acid that is cyclopentane substituted at position 1 by amino and carboxy groups.

General Description

Cycloleucine is a nonmetabolizable amino acid widely used as a building block in peptide synthesis.

Purification Methods

Any Cl -or other anions are removed by stirring with a strong cation exchange resin (Amberlite IR-120), filtering, and washing with distilled H2O until the filtrate is free from the anion. The resin is then stirred overnight with 6N NH4OH, filtered, the filtrate is decolourised (charcoal) and evaporated to dryness in a vacuum. The residue is recrystallised from H2O/EtOH. Also crystallise it from aqueous EtOH. The hydrochloride has m 222-224o(dec). [Neelakantan & Hartung J Org Chem 23 967 1958, Connors & Ross J Chem Soc 2119 1960. O’Donnell et al. Synthesis 127 1984, Beilstein 14 IV 974.]

Cycloleucine(52-52-8)Related Product Information

• 6-Aminocaproic acid
• Acetaminophen
• Cyclopentanecarboxylic acid
• Tris(hydroxymethyl)aminomethane
• Cyclopentyl chloride
• ALTRENOGEST
• Methylcyclopentane
• EC 2.6.1.2
• Cyclopentane
• Bromocyclopentane
• 3-Aminophenol
• N-CARBOBENZOXY-DL-LEUCINE
• Glycine
• 1-Aminocyclopentane-1-carboxylic acid methyl ester hydrochloride Cycloleucine Methyl Ester.HCl,CYCLOLEUCINE METHYL ESTER HCL
• BOC-CYCLOLEUCINE,N-ALPHA-T-BUTOXYCARBONYL-CYCLOLEUCINE,N-BOC-CYCLOLEUCINE
• FMOC-CYCLOLEUCINE,N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-CYCLOLEUCINE
• (1S,3R)-ACPD
• (1R,3R)-1-AMINOCYCLOPENTANE-1,3-DICARBOXYLIC ACID