D-alpha-Cyclohexylglycine Chemical Properties

Melting point:

256 °C

alpha 

-34.5 º (c=0.4 5N HCl)

Boiling point:

292.8±23.0 °C(Predicted)

Density 

1.120±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO

pka

2.44±0.10(Predicted)

form 

Solid

color 

Off-White

Water Solubility 

Soluble

BRN 

3196806

InChI

InChI=1/C8H15NO2/c9-7(8(10)11)6-4-2-1-3-5-6/h6-7H,1-5,9H2,(H,10,11)/t7-/s3

InChIKey

WAMWSIDTKSNDCU-SSDOTTSWSA-N

SMILES

C1(CCCCC1)[C@@H](N)C(=O)O |&1:6,r|

CAS DataBase Reference

14328-52-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-24/25

WGK Germany 

3

HS Code 

29224999

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

D-alpha-Cyclohexylglycine Usage And Synthesis

Description

D-alpha-Cyclohexylglycine is a kind of non-proteinogenic amino acid. It is widely presented in various natural products and pharmaceutical intermediates. It can be incorporated into the peptide inhibitors renders resistance from peptidases and proteinases and thereby imparts pharmacological stability to molecules. Some derivatives of Cyclohexylglycine has been recently been developed into inhibitors of the dipeptidyl peptidase-IV enzyme (“DP-IV inhibitors”) and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly type 2 diabetes.

References

https://www.qmbio.com/?shopp_category=chg
Edmondson, Scott D., A. Mastracchio, and E. R. Parmee. "CYCLOHEXYLGLYCINE DERIVATIVES AS DIPEPTIDYL PEPTIDASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES." (2008).
Mastracchio, Anthony, et al. "Heterocycle-Fused Cyclohexylglycine Derivatives as Novel Dipeptidyl Peptidase-IV Inhibitors. " Cheminform 35.35(2004):203-206.

Chemical Properties

white powder

Uses

D-Cyclohexylglycine (cas# 14328-52-0) is a compound useful in organic synthesis.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

The general procedure for synthesizing D-cyclohexylglycine from levophenylglycine is as follows: Example 1: Preparation of D-cyclohexylglycine 100 g (661.5 mmol) of D-phenylglycine was dissolved or suspended in a mixture of 890 ml of deionized water, 290 ml of isopropanol and 66.7 ml (802 mmol) of 37% hydrochloric acid. 10 g of Pt/Rh catalyst (4% Pt + 1% Rh loaded on activated carbon with about 50% water, corresponding to about 5 wt% of the amount of D-phenylglycine) was added. The reaction mixture was transferred to a 2 liter hydrogenation autoclave. It was displaced three times with nitrogen and then flushed twice with hydrogen, after which a hydrogen pressure of 8-10 bar was established and the reaction system was heated to 50-60°C. After about 6 to 8 hours of reaction, the hydrogen uptake was complete (theoretical H2 uptake of 44.4 L). The hydrogen was released by depressurization and again replaced three times with nitrogen. The reaction solution was filtered while hot and the catalyst was washed with 200 ml of deionized water. The filtrate was first adjusted to pH 2-2.5 with 50% sodium hydroxide solution at 40-60°C, at which point crystals began to precipitate. The pH was maintained and stirred for 15-30 min, then adjusted to pH 5-6 with 50% sodium hydroxide solution.The reaction mixture was cooled to 0-10 °C in an ice bath, the product was collected by filtration, washed with 300 ml of deionized water and dried in a vacuum oven at 50-70 °C. The catalyst can be reused for several times without any problem. The catalyst can be reused several times without deactivation. Yield: 100-102 g (95.8-97.7% yield). 1H-NMR (500 MHz, D2O/NaOD): δ (ppm) = 1-1.26 and 1.53-1.75 (both m, combined 11H, cyclohexyl proton), 3.02 (d, 1H, α-proton). The enantiomeric purity of the resulting D-cyclohexylglycine was consistent with that of the starting material D-phenylglycine by chiral GC analysis.

References

[1] Patent: WO2005/14526, 2005, A1. Location in patent: Page/Page column 12
[2] Chemische Berichte, 1986, vol. 119, # 7, p. 2191 - 2207
[3] Journal of Organic Chemistry, 1983, vol. 48, # 13, p. 2195 - 2202
[4] Justus Liebigs Annalen der Chemie, 1936, vol. 523, p. 199,203
[5] Il Farmaco; edizione scientifica, 1971, vol. 26, # 5, p. 474 - 486

D-alpha-Cyclohexylglycine(14328-52-0)Related Product Information

• Cyclohexanecarboxylic acid
• 4-Aminophenylacetic acid
• Isocyanatocyclohexane
• Folic acid
• Diethylstilbestrol
• Molasses
• Nitrilotriacetic acid
• Iminodiacetic acid
• (Aminomethyl)cyclohexane
• Cyclohexylacetic acid
• Glycine
• Hyaluronic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Sodium N-cyclohexylsulfamate
• Citric acid
• α-Lipoic Acid
• Ascoric Acid
• FMOC-D-ALPHA-CYCLOHEXYLGLYCINE,FMOC-CYCLOHEXYL-D-GLYCINE