| Identification | More | [Name]
Methyl D-valinate hydrochloride | [CAS]
7146-15-8 | [Synonyms]
D-VALINE METHYL ESTER HCL
D-VALINE METHYL ESTER HYDROCHLORIDE
D-VALINE-OME HCL
H-D-VAL-OME HCL
METHYL D-VALINATE HYDROCHLORIDE | [EINECS(EC#)]
230-454-7 | [Molecular Formula]
C6H14ClNO2 | [MDL Number]
MFCD00237309 | [Molecular Weight]
167.63 | [MOL File]
7146-15-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline | [Melting point ]
~170 °C (dec.) | [alpha ]
-15 º (c=2, H2O) | [refractive index ]
-15 ° (C=2, H2O) | [storage temp. ]
2-8°C | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [Water Solubility ]
Soluble in water | [form ]
Powder | [color ]
White | [Optical Rotation]
[α]20/D 15.5±2°, c = 2% in H2O | [BRN ]
3912091 | [Major Application]
peptide synthesis | [InChI]
InChI=1/C6H13NO2.ClH/c1-4(2)5(7)6(8)9-3;/h4-5H,7H2,1-3H3;1H/t5-;/s3 | [InChIKey]
KUGLDBMQKZTXPW-JEDNCBNOSA-N | [SMILES]
C(OC)(=O)[C@@H](C(C)C)N.[H]Cl |&1:4,r| | [CAS DataBase Reference]
7146-15-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HS Code ]
29241990 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
Crystalline | [Uses]
D-Valine methyl ester hydrochloride is a protected form of D-Valine (V094200). D-Valine (an isomer of the essential amino acid L-Valine [V094205])exhibited inhibitory effects on fibroblasts that contaminated mammalian kidney cultures, allowing for selective growth epithelial cells. D-Valine is also known for its presence in the structure of Actinomycin D, an antitumour drug. D-Valine is naturally synthesized by Streptomyces antibioticus. | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
The general procedure for the synthesis of D-valine methyl ester hydrochloride from methanol and D-valine was as follows: 8-10 mL of thionyl chloride was added slowly and dropwise to 100 mL of dry methanol suspension containing 5 g of D-valine at 0-5 °C. The reaction mixture continued to be stirred for 2 hours after the dropwise addition was completed, and was subsequently kept at 20-22°C for 24 hours to complete the reaction. After completion of the reaction, the solvent was removed by vacuum evaporation at 30-40°C. The residue was mixed with anhydrous ether and the product was separated by filtration, dried and recrystallized from the mixed methanol-ether solvent to give D-valine methyl ester hydrochloride. The yield of this synthesis step was 75% and the product had a melting point of 155-156°C and a specific spin of -15±1° (c=1.0, EtOH). Literature reports a specific spin of -15.5±2° (c=2.0,2). Infrared spectra (cm-1) showed characteristic absorption peaks located at 1730 and 1575. | [References]
[1] Tetrahedron, 1989, vol. 45, # 17, p. 5641 - 5654
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 2002, vol. 45, # 6, p. 449 - 470
[3] European Journal of Organic Chemistry, 2010, # 22, p. 4276 - 4287
[4] Journal of the American Chemical Society, 2013, vol. 135, # 19, p. 7235 - 7250
[5] Russian Journal of Bioorganic Chemistry, 2017, vol. 43, # 4, p. 456 - 462 |
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