D-Alanine Chemical Properties

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

3

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29224995

MSDS

• Language:English Provider:D-Alanine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

D-Alanine Usage And Synthesis

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.

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