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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:
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 Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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
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
D-Amino Acids: Physiology, Metabolism, and Application (2016)
Irène Amblard et al.
Communications biology, 3(1), 536-536 (2020-10-01)
Although a physiological role for redox signaling is now clearly established, the processes sensitive to redox signaling remains to be identified. Ratiometric probes selective for H2O2 have revealed its complex spatiotemporal dynamics during neural development and adult regeneration and perturbations
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