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A7377

Sigma-Aldrich

D-Alanine

≥98% (HPLC)

Synonym(s):

(R)-2-Aminopropionic acid

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About This Item

Linear Formula:
CH3CH(NH2)CO2H
CAS Number:
338-69-2
Molecular Weight:
89.09
Beilstein/REAXYS Number:
1720249
EC Number:
206-418-1
MDL number:
MFCD00008077
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24891121
NACRES:
NA.26

product name

D-Alanine, ≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

color

white

mp

291 °C (dec.) (lit.)

solubility

H2O: soluble

application(s)

detection
peptide synthesis

SMILES string

C[C@@H](N)C(O)=O

InChI

1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1

InChI key

QNAYBMKLOCPYGJ-UWTATZPHSA-N

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General description

Alanine is a non essential amino acid.

Application

D-Alanine has been used:
  • as an amine donor for ω-transaminase mediated (R)-amination
  • as a substrate for the treatment of D-amino acid oxidase (DAAO )-transfected cells
  • to measure the heat capacity of L-alanine single crystal

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).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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D-Amino Acids: Physiology, Metabolism, and Application (2016)
Heat Capacity and DC-Magnetic Susceptibility Evidence for the Asymmetry of Electron Spin-Flip Phase Transition of N+ H? O-Bond in Chiral Alanine Crystal
WANG WQ, et al.
Acta Physico-Chimica Sinica, 28(4), 773-780 (2012)
A system for omega-transaminase mediated (R)-amination using L-alanine as an amine donor
Richter N, et al.
Green Chemistry, 17(5), 2952-2958 (2015)
Srinivas Suda et al.
Journal of bacteriology, 194(3), 708-714 (2011-11-30)
Ltnα and Ltnβ are individual components of the two-peptide lantibiotic lacticin 3147 and are unusual in that, although ribosomally synthesized, they contain d-amino acids. These result from the dehydration of l-serine to dehydroalanine by LtnM and subsequent stereospecific hydrogenation to
Amit Priyadarshi et al.
Biochimica et biophysica acta, 1794(7), 1030-1040 (2009-03-31)
Alanine racemase (AlaR) is a bacterial enzyme that belongs to the fold-type III group of pyridoxal 5'-phosphate (PLP)-dependent enzymes. AlaR catalyzes the interconversion between L- and D-alanine, which is important for peptidoglycan biosynthesis. This enzyme is common in prokaryotes, but
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