AC-D-ALA-OH

AC-D-ALA-OH Property

Melting point:

125 °C

Boiling point:

369.7±25.0 °C(Predicted)

Density 

1.170

storage temp. 

-20°C

solubility 

Soluble in water or 1% acetic acid

pka

3.69±0.10(Predicted)

form 

Solid

color 

White to off-white

Water Solubility 

Slightly soluble in water.

InChIKey

KTHDTJVBEPMMGL-VKHMYHEASA-N

LogP

-1.638 (est)

Safety

WGK Germany 

3

HS Code 

2922498590

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

AC-D-ALA-OH Chemical Properties,Usage,Production

Chemical Properties

White crystal powder

Uses

N-Acetyl-D-alanine may be used with other D-aminoacylated amino acids as a substrate for the identification, differentiation and characterization of D-aminoacylase(s)/amidohydrolase(s). N-acetyl-D-alanine may be used to study aglycon pocket specific binding on vancomycin.

Biochem/physiol Actions

N-Acetyl-D-alanine may be used with other D-aminoacylated amino acids as a substrate for the identification, differentiation and characterization of D-aminoacylase(s)/amidohydrolase(s). N-acetyl-D-alanine may be used to study aglycon pocket specific binding on vancomycin.

Synthesis

The general procedure for the synthesis of N-acetyl-D-alanine from 2-acetamidoacrylic acid is as follows: the substrate (Eq. 3), enantiomeric excess (ee), and absolute stereoconfigurations of the chiral products (Eq. 2) prepared by asymmetric hydrogenation using a chiral catalyst precursor are listed in Table 3. The catalyst precursor was (S)-(+)-(2-{[(di-tert-butyl)-[phosphinylidene]-methyl]-methyl-phosphinyl}-2-methyl-propyl)-(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate (Eq. 23). For each entry in Table 3, the catalyst precursor (0.01 mmol) was dissolved in degassed methanol (1 mL) in a Griffin-Worden pressure vessel equipped with the accessories required for connection to a hydrogen cylinder. The substrate (1 mmol) was first dissolved in methanol (4 mL) and then delivered via syringe into the catalyst-methanol solution. The vessel was sealed and pressurized to 50 psi H2. The time to completion of the reaction was determined by monitoring the cessation of H2 gas absorption. Table 3: Enantioselectivity of chiral compounds prepared by asymmetric hydrogenation of prechiral substrates (Formula 2) (Formula 3) Example R1 R2 R3 R4 X ee Configuration.5 AcNH H H CO2H >99% R 6 AcNH Ph H H CO2H >99% R 7 AcNH H H CO2Me >99% R 8 AcNH Ph H H CO2Me >99% R 9 AcNH - C5H10- CO2Me 99% R For each reaction shown in Table 3, the enantiomeric excess was determined by chiral gas chromatography (GC) or chiral high performance liquid chromatography (HPLC). Table 4 provides details of the ee determination methods. To determine the ee of N-acetylalanine (Example 5) and N-acetylphenylalanine (Example 6), each compound was treated with trimethylsilyl diazomethane, which was converted to its corresponding methyl ester, and analyzed as described in Example 7 or Example 8, respectively. Absolute stereochemical configurations were determined by comparing the sign of the spinodal and literature values: (S)-N-acetylalanine methyl ester [α]20D = -91.7° (c 2, H2O), JP Wolf III C. Neimann, Biochemistry 2: 493 (1963); (S)-N-acetylphenylalanine methyl ester [α]20D = + 16.4° (c 2, MeOH), B.D. Vineyard et al, J. Am. Chem. Soc. 99: 5946 (1997); (S)-N-acetylcyclohexylglycine methyl ester [α]20D = -4.6° (c = 0.13, EtOH), M.J. Burk et al, J. Am. Chem. Soc. 117: 9375 (1995). Table 4: Conditions for Enantiomeric Excess Determination Example Method Column Mobile Phase Flow Rate Column Temperature Concentration Retention Time-R Retention Time-S5 Capillary GC Chrompack Chiral-Daicel - - 120°C - 10.5 min 11.0 min 6 HPLC Chiralcel OJ 10% IPA/hexane 1 mL/min 30°C 2 mg/mL 11.6 min 17.7 min9 Capillary GC Chirasil-L-Val - - 145°C - 11.3 min 12.0 min

References

[1] Advanced Synthesis and Catalysis, 2003, vol. 345, # 1-2, p. 308 - 323
[2] Angewandte Chemie, 1987, vol. 99, # 9, p. 921 - 922
[3] Tetrahedron Letters, 1984, vol. 25, # 43, p. 4965 - 4966
[4] Journal of Organic Chemistry, 1980, vol. 45, # 23, p. 4728 - 4739
[5] Journal of the American Chemical Society, 1981, vol. 103, # 9, p. 2273 - 2280