56246
cis-4-Hydroxy-D-proline
≥99.0% (NT)
Synonym(s):
(2R,4R)-(+)-4-Hydroxy-2-pyrrolidinecarboxylic acid, D-allo-Hydroxyproline
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About This Item
Empirical Formula (Hill Notation):
C5H9NO3
CAS Number:
Molecular Weight:
131.13
EC Number:
219-963-5
UNSPSC Code:
12352200
MDL number:
Beilstein/REAXYS Number:
81439
assay
≥99.0% (NT)
optical activity
[α]20/D +60±1°, c = 1% in H2O
mp
243 °C (dec.) (lit.)
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-QWWZWVQMSA-N
Biochem/physiol Actions
Cis-4-hydroxy-D-proline is a pharmaceutically active, anti-convulsive, amino acid transported by the proton coupled amino acid transporter (PAT1) expressed in intestine and brain. Cis-4-hydroxy-D-proline upregulates the expression of the hydroxyproline transporter hypM in legume endosymbiont Sinorhizobium meliloti.
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Allyson M Maclean et al.
Molecular plant-microbe interactions : MPMI, 22(9), 1116-1127 (2009-08-07)
Hydroxyproline-rich proteins in plants offer a source of carbon and nitrogen to soil-dwelling microorganisms in the form of root exudates and decaying organic matter. This report describes an ABC-type transport system dedicated to the uptake of hydroxyproline in the legume
Linda Metzner et al.
The Journal of pharmacology and experimental therapeutics, 309(1), 28-35 (2004-01-14)
Several proline derivatives such as L-azetidine-2-carboxylic acid, cis-4-hydroxy-L-proline, and 3,4-dehydro-DL-proline prevent procollagen from folding into a stable triple-helical conformation, thereby reducing excessive deposition of collagen in fibrotic processes and the growth of tumors. This study was performed to investigate whether
S Sarhan et al.
General pharmacology, 20(1), 53-60 (1989-01-01)
1. The anticonvulsant properties of L-proline, of proline derivatives (trans-4-hydroxy-L-proline, cis-4-hydroxy-D-proline, 3,4-dehydro-D,L-proline) and of D- and L-pipecolic acid were studied alone and in combination with vigabatrin (R/S-4-aminohex-5-enoic acid). 3-Mercaptopropionic acid and pentylenetetrazol-induced convulsions in mice were used as animal models
L Metzner et al.
Amino acids, 31(2), 111-117 (2006-05-16)
The proton coupled amino acid transporter PAT1 expressed in intestine, brain, and other organs accepts L- and D-proline, glycine, and L-alanine but also pharmaceutically active amino acid derivatives such as 3-amino-1-propanesulfonic acid, L-azetidine-2-carboxylic acid, and cis-4-hydroxy-D-proline as substrates. We systematically
Iris Thondorf et al.
Bioorganic & medicinal chemistry, 19(21), 6409-6418 (2011-10-01)
The proton-coupled amino acid transporter hPAT1 has recently gained much interest due to its ability to transport small drugs thereby allowing their oral administration. A three-dimensional quantitative structure-activity relationship (3D QSAR) study has been performed on its natural and synthetic
Global Trade Item Number
| SKU | GTIN |
|---|---|
| CDS025240-100MG | 04065269020899 |
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