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Sigma-Aldrich

trans-4-Hydroxy-L-proline

BioXtra, ≥99.0% (NT)

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Synonym(s):
(2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid, Hyp
Empirical Formula (Hill Notation):
C5H9NO3
CAS Number:
Molecular Weight:
131.13
Beilstein:
81441
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.26

product line

BioXtra

Quality Level

Assay

≥99.0% (NT)

form

solid

optical activity

[α]20/D −76.0±1.5°, c = 5% in H2O

impurities

≤0.3% foreign amino acids

ign. residue

≤0.1% (as SO4)

loss

≤0.1% loss on drying, 110 °C

color

colorless to white

mp

273 °C (dec.) (lit.)

anion traces

chloride (Cl-): ≤100 mg/kg
sulfate (SO42-): ≤100 mg/kg

cation traces

Ca: ≤10 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤5 mg/kg
K: ≤50 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
NH4+: ≤100 mg/kg
Na: ≤50 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Zn: ≤5 mg/kg

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+/m1/s1

InChI key

PMMYEEVYMWASQN-DMTCNVIQSA-N

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Biochem/physiol Actions

Trans-4-Hydroxy-L-proline is used as a starting material in the synthesis of (-)-secrinine; the synthesis of prolinol-based nucleotide analogues with N-phosphonomethyl moiety attached to the nitrogen atom of prolinol ring and in asymmetric synthesis of the ABC-ring system of the antitumor antibiotic MPC1001.
Trans-4-Hydroxy-L-proline is used in the organic synthesis of depsilairdin analogues, noncompetitive peptidomimetic inhibitors of multidrug resistance P-glycoprotein and 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analogues.

Other Notes

Natural constituent of animal structural proteins such as collagen and elastin.
Enzymes and intermediates of hydroxyproline degradation

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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E. Adams
Methods in Enzymology, 17B, 266-266 (1971)
Hsuan-Shu Lee et al.
Journal of gastroenterology and hepatology, 20(7), 1109-1114 (2005-06-16)
Needle liver biopsy is essential for the diagnosis of liver fibrosis and cirrhosis. However, sampling variability has been reported by semiquantitative methods. The aim of the present study was to investigate quantitatively the sampling variability of needle liver biopsy on
Ville V Meretoja et al.
Biomaterials, 34(17), 4266-4273 (2013-03-16)
In this work, we investigated the effects of lowered oxygen tension (20% and 5% O2) on the chondrogenesis and hypertrophy of articular chondrocytes (ACs), mesenchymal stem cells (MSCs) and their co-cultures with a 30:70 AC:MSC ratio. Cells were cultured for
Mari Ogawa-Ohnishi et al.
Nature chemical biology, 9(11), 726-730 (2013-09-17)
Hydroxyproline (Hyp) O-arabinosylation is a post-translational modification that is prominent in extracellular glycoproteins in plants. Hyp O-arabinosylation is generally found in these glycoproteins in the form of linear oligoarabinoside chains and has a key role in their function by contributing
Massimo Petrera et al.
Arthroscopy : the journal of arthroscopic & related surgery : official publication of the Arthroscopy Association of North America and the International Arthroscopy Association, 29(10), 1685-1692 (2013-10-01)
This study aimed to determine the effects of platelet-rich plasma (PRP) on the histologic, biochemical, and biomechanical properties of tissue-engineered cartilage. Chondrocytes isolated from bovine metacarpal-phalangeal articular cartilage were seeded on top of a porous ceramic substrate (calcium polyphosphate [CPP]).

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