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Key Documents

H1637

Sigma-Aldrich

cis-4-Hydroxy-L-proline

collagen synthesis inhibitor

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C5H9NO3
CAS Number:
Molecular Weight:
131.13
Beilstein:
81440
EC Number:
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26

Quality Level

Assay

≥98% (TLC)

form

powder

technique(s)

ligand binding assay: suitable

color

white to faint yellow

mp

257 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

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

InChI key

PMMYEEVYMWASQN-IMJSIDKUSA-N

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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.

Biochem/physiol Actions

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.

Other Notes

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

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

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