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Sigma-Aldrich

trans-4-Hydroxy-L-proline

≥99.0% (NT), BioXtra

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Synonym(s):
(2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid, Hyp
Empirical Formula (Hill Notation):
C5H9NO3
CAS Number:
51-35-4
Molecular Weight:
131.13
Beilstein:
81441
EC Number:
200-091-9
MDL number:
MFCD00064320
UNSPSC Code:
12352209
PubChem Substance ID:
57651574
NACRES:
NA.26

product line

BioXtra

Quality Level

100

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

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
Jacob Kofoed et al.
Chemical communications (Cambridge, England), (14)(14), 1482-1484 (2006-04-01)
The aldol reaction of acetone with aldehydes in aqueous medium under catalysis by zinc-proline (Zn(L-Pro)2) and secondary amines such as proline, (2S,4R)-4-hydroxyproline (Hyp) and (S)-(+)-1-(2-pyrrolidinomethyl)pyrrolidine (PMP) is shown to proceed by an enamine mechanism, as evidenced by reductive trapping of
Shahrzad Hosseininia et al.
BMC musculoskeletal disorders, 14, 18-18 (2013-01-11)
It remains to be shown whether OA shares molecular similarities between different joints in humans. This study provides evidence for similarities in cartilage molecular damage in osteoarthritic (OA) joints. Articular cartilage from osteoarthritic hip joints were analysed and compared to
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