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C9650

Sigma-Aldrich

β-Cyano-L-alanine

≥95%, suitable for ligand binding assays

Synonym(s):

3-cyano-L-alanine

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About This Item

Empirical Formula (Hill Notation):
C4H6N2O2
CAS Number:
6232-19-5
Molecular Weight:
114.10
MDL number:
MFCD00021722
UNSPSC Code:
12352209
PubChem Substance ID:
24893182
NACRES:
NA.26

product name

β-Cyano-L-alanine, ≥95%

assay

≥95%

form

powder

technique(s)

ligand binding assay: suitable

color

white

mp

217 °C

storage temp.

−20°C

SMILES string

OC([C@@H](N)CC#N)=O

InChI

1S/C4H6N2O2/c5-2-1-3(6)4(7)8/h3H,1,6H2,(H,7,8)/t3-/m0/s1

InChI key

BXRLWGXPSRYJDZ-VKHMYHEASA-N

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Biochem/physiol Actions

β-Cyano-L-alanine (BCA) is used as a cystathione γ-lyase (CSE) inhibitor to study the physiological roles of hydrogen sulfide in processes such as angiogenesis and hypertension.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Andrew J M Howden et al.
The Plant journal : for cell and molecular biology, 57(2), 243-253 (2008-09-13)
Pseudomonas fluorescens SBW25 is a plant growth-promoting bacterium that efficiently colonizes the leaf surfaces and rhizosphere of a range of plants. Previous studies have identified a putative plant-induced nitrilase gene (pinA) in P. fluorescens SBW25 that is expressed in the
Markus Piotrowski et al.
Plant molecular biology, 61(1-2), 111-122 (2006-06-21)
Cyanoalanine hydratase (E.C. 4.2.1.65) is an enzyme involved in the cyanide detoxification pathway of higher plants and catalyzes the hydrolysis of beta-cyano-L-alanine to asparagine. We have isolated the enzyme from seedlings of blue lupine (Lupinus angustifolius) to obtain protein sequence
Andrew G S Warrilow et al.
Journal of experimental botany, 53(368), 439-445 (2002-02-16)
The reaction mechanisms of three enzymes belonging to a single gene family are compared: a cyanoalanine synthase and two isoforms of O-acetylserine (thiol) lyase (O-ASTL) isolated from spinach (Spinacea oleracea L. cv. Medina). O-ASTL represents a major regulatory point in
B Teague et al.
British journal of pharmacology, 137(2), 139-145 (2002-09-05)
1. Sodium hydrogen sulphide (NaHS), a donor of hydrogen sulphide (H(2)S), produced dose-related relaxation of the rabbit isolated ileum (EC(50), 76.4+/-7.9 microM) and rat vas deferens (EC(50), 64.8+/-5.4 microM) and reduced ACh-mediated contraction of the guinea-pig isolated ileum. 2. NaHS
R Miura et al.
Journal of biochemistry, 87(5), 1469-1481 (1980-05-01)
The reaction of D-amino acid oxidase [EC 1.4.3.3] (DAO) from porcine kidney with beta-cyano-D-alanine (D-BCNA) was studied. DAO was found to catalyze elimination of the cyano group as well as oxidation of D-BCNA. During the course of the reaction in
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