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T27502

Sigma-Aldrich

L-4-Thiazolidinecarboxylic acid

98%

Synonym(s):

L-Thiaproline

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About This Item

Empirical Formula (Hill Notation):
C4H7NO2S
CAS Number:
34592-47-7
Molecular Weight:
133.17
Beilstein:
81065
EC Number:
252-106-3
MDL number:
MFCD00005212
UNSPSC Code:
12352106
PubChem Substance ID:
24900069
NACRES:
NA.22

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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Application

Used in peptide coupling reactions.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL3512
MKCG1270
MKBW6578V
MKBS3596V
S75873V

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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
Khalid Mohammed Khan et al.
Molecular diversity, 10(2), 223-231 (2006-05-20)
By using internal combinatorial library we were able to identify (4R)-thiazolidines carboxylic acid and its 2-substituted analogs as active inhibitors of urease. Molecular modeling and virtual screening were utilized to find out potential compounds. Computational techniques were employed at database
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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