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