2521-86-0

Basic information

• Product Name: D-Cyclopentylglycine
• Synonyms: (R)-AMINO-CYCLOPENTYL-ACETIC ACID;D-CYCLOPENTYL GLYCINE;D-BETA-CYCLOPENTYLGLYCINE;H-D-CYCPENTGLY-OH;H-D-GLY(CYCLOPENTYL)-OH;D-CYCLOPENTYLGLYCINE 98%;H-D-Cpg-OH;(R)-2-amino-2-cyclopentylacetic acid
• CAS NO: 2521-86-0
• Molecular Formula: C₇H₁₃NO₂
• Molecular Weight: 143.18
• Product Categories: pharmacetical;Amino Acid Derivatives;a-amino;Non-natural amino acids
• Mol File: 2521-86-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 276.559oC at 760 mmHg
• Flash Point: 121.059oC
• Appearance: /
• Density: 1.168g/cm3
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.522
• Storage Temp.: Store at 0°C
• PKA: 2.49±0.10(Predicted)
• CAS DataBase Reference: D-Cyclopentylglycine(CAS DataBase Reference)
• NIST Chemistry Reference: D-Cyclopentylglycine(2521-86-0)
• EPA Substance Registry System: D-Cyclopentylglycine(2521-86-0)

Safety Data

• Hazardous Substances Data: 2521-86-0(Hazardous Substances Data)

Usage

Uses

D-Cyclopentylglycine

InChI:InChI=1/C7H13NO2/c8-6(7(9)10)5-3-1-2-4-5/h5-6H,1-4,8H2,(H,9,10)/t6-/m1/s1

Upstream product

• 145275-92-9 2-Amino-2-cyclopentyl-N-methoxyacetamide 
• 936448-97-4 2-((Benzyloxycarbonyl)amino)-2-(2-cyclopentenyl)-N-methoxyacetamide 
• 14579-08-9 3-trimethylsilylcyclopent-1-ene 
• 933-95-9 cyclopentylglycine 
• 2521-85-9 (+)-(2R)-N-Acetyl-2-cyclopentylglycin 

Downstream Products

• 156881-63-9 (R)-2-((tertbutoxycarbonyl)amino)-2-cyclopentylacetic acid 

Relevant articles and documents

Amine-boranes: Effective reducing agents for the deracemisation of DL-amino acids using L-amino acid oxidase from Proteus myxofaciens

The deracemisation of DL-α-amino acids using L-amino acid oxidase from Proteus myxofaciens and amine-boranes as chemical reducing agents has been investigated. Amine-boranes were found to be of particular interest in terms of reactivity and chemoselectivity compared to sodium borohydride and cyanoborohydride. Starting from the racemate, a range of D-amino acids were obtained in yields of up to 90% and e.e. >99%.

Synthesis of Racemic α-Amino Carboxamides via Lewis Acid-Mediated Reactions of α-Methoxyglycinamide Derivatives with Allylsilanes: Enzymatic Resolution to Optically Active α-Amino Acids

A short and expedient synthetic route to optically active, saturated and γ,δ-unsaturated α-amino acids is reported.The key step is a BF3*Et2O-mediated reaction of allylsilanes with N-(alkoxycarbonyl)-α-methoxyglycinamides 11-15, leading to the corresponding γ,δ-unsaturated α-aminocarboxamides.The genuine SN1-character of this process with iminium ion 6 as intermediate is proven in the case of the glycine ester 10.Thus, reaction of enzymatically resolved 10 with ?-nucleophiles leads to racemic products.The most useful iminium precursors are the N-methoxyamides 12-14 providing good yields of coupling products.The most convenient N-protective group is the allyloxycarbonyl group.Deprotection proceeds via a Pd(O)-catalyzed transprotection to the corresponding BOC-protected analogues.Four examples of the enzymatic resolution of α-amino carboxamides, by using an L-specific aminopeptidase from Pseudomonas putida, are described in detail.Most notably, secondary N-methoxyamides are good substrates for the enzyme to provide the desired α-amino acids in high optical purity.