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88424

Sigma-Aldrich

3-(2-Thienyl)-L-alanine

≥98.0% (TLC)

Synonym(s):

(S)-α-Amino-2-thiophenepropionic acid, (S)-2-Amino-3-(2-thienyl)propionic acid

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About This Item

Empirical Formula (Hill Notation):
C7H9NO2S
CAS Number:
22951-96-8
Molecular Weight:
171.22
Beilstein:
82872
MDL number:
MFCD00064335
UNSPSC Code:
12352209
PubChem Substance ID:
57653304
NACRES:
NA.22

Assay

≥98.0% (TLC)

form

powder

optical activity

[α]20/D −30.5±1.5°, c = 1% in H2O

reaction suitability

reaction type: solution phase peptide synthesis

mp

255-263 °C (dec.) (lit.)
~260 °C (dec.)

application(s)

peptide synthesis

SMILES string

N[C@@H](Cc1cccs1)C(O)=O

InChI

1S/C7H9NO2S/c8-6(7(9)10)4-5-2-1-3-11-5/h1-3,6H,4,8H2,(H,9,10)/t6-/m0/s1

InChI key

WTOFYLAWDLQMBZ-LURJTMIESA-N

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Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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Arginine European Pharmacopoeia (EP) Reference Standard

A1270000

Arginine

3,4-Dihydroxy-L-phenylalanine ≥98% (TLC)

Sigma-Aldrich

D9628

3,4-Dihydroxy-L-phenylalanine

L-Alanine ≥98% (TLC)

Sigma-Aldrich

A7627

L-Alanine

D P Bedard et al.
Journal of bacteriology, 141(1), 100-105 (1980-01-01)
When treated with the amino acid analog beta-2-DL-thienylalanine, cells of the yeast Saccharomyces cerevisiae accumulated in the G1 portion of the cell cycle at the "start" event. This G1 arrest was accompanied by a rapid decrease in the rate of
"Physiological phenylketonuria": a biochemical defect caused by delayed maturation of the phenylalanine hydroxylation pathway and by competition with the phenylalanine biosynthetic pathway.
K J Brown
Medical hypotheses, 6(2), 215-224 (1980-02-01)
G Riccardi et al.
Journal of bacteriology, 147(3), 1002-1007 (1981-09-01)
Mutants of Spirulina platensis resistant to 5-fluorotryptophan, beta-3-thienyl-alanine, ethionine, p-fluorophenylalanine, or azetidine-2-carboxylic acid were isolated. Some of these mutants appeared to be resistant to more than one analog and to overproduce the corresponding amino acids. A second group was composed
Uptake and incorporation of amino acids by suspension cultured mammalian cells: a comparative study involving eleven naturally-occurring and four analogue amino acids.
D N Wheatley et al.
Cytobios, 30(118), 101-126 (1981-01-01)
K J Brown et al.
Medical microbiology and immunology, 168(1), 11-24 (1980-02-01)
Faecal samples were taken from three diet-managed phenylketonuric children to determine effects of beta-2-thienylalanine (beta-2-t) on indigenous bacteria. From sample swabs, 127 anaerobes were identified and tested for beta-2-t inhibition on a phenylalanine (Phe)-free medium, Anaerobe Inhibition Test (AIT) agar.
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