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H1637

Sigma-Aldrich

cis-4-Hydroxy-L-proline

collagen synthesis inhibitor

Synonyme(s) :

(2S,4S)-(−)-4-Hydroxy-2-pyrrolidinecarboxylic acid, CHP

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About This Item

Formule empirique (notation de Hill):
C5H9NO3
Numéro CAS:
618-27-9
Poids moléculaire :
131.13
Numéro Beilstein :
81440
Numéro CE :
210-542-1
Numéro MDL:
MFCD00064319
Code UNSPSC :
12352209
eCl@ss :
32160406
ID de substance PubChem :
24895470
Nomenclature NACRES :
NA.26

Niveau de qualité

100

Pureté

≥98% (TLC)

Forme

powder

Technique(s)

ligand binding assay: suitable

Couleur

white to faint yellow

Pf

257 °C (dec.) (lit.)

Application(s)

peptide synthesis

Chaîne SMILES 

O[C@@H]1CN[C@@H](C1)C(O)=O

InChI

1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m0/s1

Clé InChI

PMMYEEVYMWASQN-IMJSIDKUSA-N

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Catégories apparentées

Application

cis-4-Hydroxy-L-proline (CHP) is a proline analog that inhibits collagen synthesis and has been used as an anticancer compound. CHP blocked myotube formation and expression of sarcomeric myosin heavy chain in C2C12 murine skeletal muscle cells. CHP inhibited proliferation of murine Panc02 pancreatic carcinoma cell line and rat pancreatic carcinoma cell line DSL6A.

Actions biochimiques/physiologiques

cis-4-Hydroxy-L-proline (CHP) and its derivatives may have anticancer activity. cis-4-Hydroxy-L-proline and other hydrosyl-L-prolines are important intermediates for chiral synthesis of potential drugs.

Autres remarques

Constituent of Amanita sp. peptide toxins but not of animal proteins like collagen.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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trans-4-Hydroxy-L-proline analytical standard

Supelco

41875

trans-4-Hydroxy-L-proline

N-Boc-cis-4-hydroxy-L-proline methyl ester 97%

Sigma-Aldrich

654000

N-Boc-cis-4-hydroxy-L-proline methyl ester

Z-Hyp-OH ≥99.0% (T)

Sigma-Aldrich

96310

Z-Hyp-OH

Ryotaro Hara et al.
Biochemical and biophysical research communications, 379(4), 882-886 (2009-01-10)
Hydroxyprolines are valuable chiral building blocks for organic synthesis of pharmaceuticals. Several microorganisms producing L-proline trans-4- and cis-3-hydroxylase were discovered and these enzymes were applied to the industrial production of trans-4- and cis-3-hydroxy-L-proline, respectively. Meanwhile, other hydroxyproline isomers, cis-4- and
Dietrich Sturm et al.
International journal of colorectal disease, 25(8), 921-929 (2010-04-21)
This study addressed the question of whether the collagen metabolism modulator cis-4-Hydroxy-L-proline (CHP) is applicable for potential use as a therapeutic inhibitor of pancreatic carcinoma cell growth. Cell proliferation, as well as quantification of apoptosis of murine Panc02 cells, was
Christoph Mueller et al.
World journal of gastroenterology, 12(10), 1569-1576 (2006-03-30)
To investigate the biological effects of cis-hydroxyproline (CHP) on the rat pancreatic carcinoma cell line DSL6A, and to examine the underlying molecular mechanisms. The effect of CHP on DSL6A cell proliferation was assessed by using BrdU incorporation. The expression of
Heather Dickens et al.
Molecular medicine reports, 1(4), 459-464 (2008-07-01)
cis-4-Hydroxy-L-proline (CHP) is being clinically evaluated as an anticancer drug. Since this compound targets the production of L-proline-rich proteins and critical L-proline residues, its impact on long-term cultures of human hepatocytes and toxicity in rats was studied to investigate possible
Sevil Oskay Halacli et al.
Clinical immunology (Orlando, Fla.), 161(2), 316-323 (2015-06-29)
Combined immunodeficiencies (CIDs) are heterogeneous group of disorders characterized by abrogated/impaired T cell development and/or functions that resulted from diverse genetic defects. In addition to the susceptibility to infections with various microorganisms, the patients may have lymphoproliferation, autoimmunity, inflammation, allergy
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