D-Alanine Property

Melting point:

291 °C (dec.)(lit.)

alpha 

-14.5 º (c=10, 6N HCl)

Boiling point:

212.9±23.0 °C(Predicted)

Density 

1.4310 (estimate)

refractive index 

-14 ° (C=2, 6mol/L HCl)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

H2O: soluble

form 

Crystalline Powder or Crystals

pka

2.31±0.10(Predicted)

color 

White to off-white

Odor

odorless

Water Solubility 

155 g/L (20 ºC)

Merck 

14,204

BRN 

1720249

LogP

-0.574 (est)

CAS DataBase Reference

338-69-2(CAS DataBase Reference)

NIST Chemistry Reference

D-Alanine(338-69-2)

EPA Substance Registry System

D-Alanine (338-69-2)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

3

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29224995

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

D-Alanine Chemical Properties,Usage,Production

Chemical Properties

A white crystalline Powder with no peculiar smell and a sweet taste. It is easily soluble in water, slightly soluble in ethanol, and insoluble in acetone and ether. The decomposition point is 297°C. The specific rotation is [α]25D -1.8° (0.5–2.0 mg/ml, H2O) and [α]25D -14.6° (0.5–2.0 mg/ml, 5 mol/L HCl).

Uses

D-Alanine is essential for the biosynthesis of peptidoglycan crosslinking sub-units that are used for bacterial cell walls.

Application

D-Alanine is a LHRH-antagonists, e.g., Abarelix (antineoplas- tic)

Definition

ChEBI: D-alanine is the D-enantiomer of alanine. It has a role as a human metabolite, an EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor and an Escherichia coli metabolite. It is a D-alpha-amino acid and an alanine. It is a conjugate base of a D-alaninium. It is a conjugate acid of a D-alaninate. It is an enantiomer of a L-alanine. It is a tautomer of a D-alanine zwitterion.

Preparation

D-Alanine can be obtained by hydrolysis and refining of proteins such as gelatin, sericin and corn protein, or it can be synthesized by chemical methods.

General Description

Alanine is a non essential amino acid.

Biochem/physiol Actions

D-Alanine is the non-proteinogenic form of alanine which is used in bacterial cell wall biosynthesis. D-Alanine is used to study the specificity and kinetics of alanine racemase(s) (alaR).

Purification Methods

Crystallise alanine from H2O or aqueous EtOH, i.e. crystallise it from 25% EtOH in water, or recrystallise it from 62.5% EtOH, wash it with EtOH and dry it to constant weight in vacuo over P2O5. [Gutter & Kegeles J Am Chem Soc 75 3893 1953, Walsh J Biol Chem 264 2394 1989.] 2,2'-Iminodipropionic acid is a likely impurity. [Beilstein 4 IV 2480. 2481.]

References

[1] ISAO UMEMURA. d-Alanine production from dl-alanine by Candida maltosa with asymmetric degrading activity[J]. Applied Microbiology and Biotechnology, 1992, 36 6: 722-726. DOI:10.1007/BF00172182.
[2] TIAN (AUTUMN) QIU. Biodistribution and racemization of gut-absorbed l/d-alanine in germ-free mice[J]. Communications Biology, 2023: 1-11. DOI:10.1038/s42003-023-05209-y.
[3] AMIT PRIYADARSHI . Structural insights into the alanine racemase from Enterococcus faecalis[J]. Biochimica et biophysica acta. Proteins and proteomics, 2009, 1794 7: Pages 1030-1040. DOI:10.1016/j.bbapap.2009.03.006.
[4] CINDY J. LEE   Jonathan V S Tian A Qiu. d-Alanine: Distribution, origin, physiological relevance, and implications in disease[J]. Biochimica et biophysica acta. Proteins and proteomics, 2020, 1868 11: Article 140482. DOI:10.1016/j.bbapap.2020.140482.