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T27502

Sigma-Aldrich

L-4-Thiazolidinecarboxylic acid

98%

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Synonym(s):
L-Thiaproline
Empirical Formula (Hill Notation):
C4H7NO2S
CAS Number:
Molecular Weight:
133.17
Beilstein/REAXYS Number:
81065
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

form

powder

optical activity

[α]20/D −141°, c = 1.3 in H2O

reaction suitability

reaction type: solution phase peptide synthesis

color

white

mp

190-200 °C (dec.) (lit.)

SMILES string

OC(=O)[C@@H]1CSCN1

InChI

1S/C4H7NO2S/c6-4(7)3-1-8-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1

InChI key

DZLNHFMRPBPULJ-VKHMYHEASA-N

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This Item
B2129A3506D9628
L-4-Thiazolidinecarboxylic acid 98%

T27502

L-4-Thiazolidinecarboxylic acid

L-Aspartic acid β-benzyl ester

B2129

L-Aspartic acid β-benzyl ester

L-(−)-Arabitol ≥98% (GC)

A3506

L-(−)-Arabitol

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

D9628

3,4-Dihydroxy-L-phenylalanine

assay

98%

assay

≥98%

assay

≥98%

assay

≥98% (TLC)

color

white

color

white

color

white

color

white to off-white

optical activity

[α]20/D −141°, c = 1.3 in H2O

optical activity

-

optical activity

-

optical activity

-

mp

190-200 °C (dec.) (lit.)

mp

225 °C

mp

101-104 °C (lit.)

mp

276-278 °C (lit.)

reaction suitability

reaction type: solution phase peptide synthesis

reaction suitability

-

reaction suitability

-

reaction suitability

-

Application

Used in peptide coupling reactions.

pictograms

Skull and crossbones

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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Bioorganic & Medicinal Chemistry Letters, 4, 887-887 (1994)
Florine Cavelier et al.
Journal of peptide science : an official publication of the European Peptide Society, 12(10), 621-625 (2006-06-21)
As proline plays an important role in biologically active peptides, many analogues of this residue have been developed to modulate the proportion of cis and trans conformers. A correlation between the pyrrolidine ring shape and structural properties of proline has
Anahí Magdaleno et al.
PloS one, 4(2), e4534-e4534 (2009-02-21)
It is well established that L-proline has several roles in the biology of trypanosomatids. In Trypanosoma cruzi, the etiological agent of Chagas' disease, this amino acid is involved in energy metabolism, differentiation processes and resistance to osmotic stress. In this
Zhong-Cheng Song et al.
European journal of medicinal chemistry, 44(10), 3903-3908 (2009-05-09)
Nine 2-arylthiazolidine-4-carboxylic acid derivatives and nine 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acid derivatives were synthesized to screen for their antibacterial activities. Compounds 5, 14-18 were first reported. Their chemical structures were clearly determined by (1)H NMR, (13)C NMR, ESI mass spectra and elemental analyses
Rajani Korukonda et al.
Journal of medicinal chemistry, 49(17), 5282-5290 (2006-08-18)
Calpain is a cytosolic cysteine endopeptidase that has been implicated in a number of disorders including cancer. We have synthesized and studied the mu-calpain inhibitory activity and cytotoxicity of peptidyl aldehydes and peptidyl alpha-ketoamides with N-substituted D-proline or L-thiaproline residues

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