| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
trans-D-4-Hydroxyproline does not have a known biological target. It may be incorporated into peptides to confer proteolytic stability, induce polyproline II helices, or increase water solubility. The hydroxyl group (trans configuration) can be further functionalized (e.g., glycosylation, phosphorylation). It is also a precursor for the synthesis of chiral pharmaceuticals, including anti-HIV agents and renin inhibitors.
|
|---|---|
| ln Vitro |
In vitro, the compound is not biologically active itself. Peptides containing D-Hyp residues have been developed as inhibitors of matrix metalloproteinases (MMPs, IC₅0 low nM) and as angiotensin-converting enzyme (ACE) inhibitors. For chemical synthesis, trans-D-Hyp is used as a building block. Not applicable.
|
| ln Vivo |
Not applicable; the compound is not used in vivo. The final peptide (e.g., an MMP inhibitor) may be evaluated in animal models for therapeutic efficacy.
|
| Enzyme Assay |
Not applicable; the compound is a synthetic intermediate. For quality control, purity is assessed by HPLC (>98%). The compound is characterized by ¹H NMR (delta 2.0-2.3 ppm (CH2), 3.2-3.5 ppm (CH2), 4.3-4.5 ppm (CH), 4.5-4.7 ppm (CH-OH)), ¹3C NMR, and mass spectrometry (m/z 132 [M+H]+). Specific rotation: [alpha]2⁰ᴅ = +45deg to +55deg (c=1, H2O). Solubility: water (50 mg/mL) and DMSO. For peptide synthesis, the N-Fmoc derivative is used in SPPS. The hydroxyl group can be protected with tBu ether (acid-labile) or TBDMS (orthogonal).
|
| Cell Assay |
Not applicable; used in chemical synthesis, not in cell-based assays. The final peptide may be tested in cells for MMP inhibition (e.g., zymography) or cell migration (scratch assay).
|
| Animal Protocol |
Not applicable; not administered to animals.
|
| ADME/Pharmacokinetics |
Not applicable; not for in vivo administration.
|
| Toxicity/Toxicokinetics |
Low toxicity. Acute oral LD₅0 >2000 mg/kg. May cause skin and eye irritation. Use PPE. Not a drug.
|
| References | |
| Additional Infomation |
(2R,4S)-4-hydroxypyrrolidine-2-carboxylic acid is a 4-hydroxy-D-proline, where the hydroxyl group at position 4 has an S configuration. Trans-4-hydroxy-D-proline has been reported in snapdragons, and relevant data are available for reference.
trans-D-4-Hydroxyproline is a research building block for peptidomimetic and pharmaceutical synthesis. It is not an FDA-approved drug. The 4-hydroxy group and D-configuration confer resistance to proteases and the ability to form stable polyproline II helices. For research use only. |
| Molecular Formula |
C5H9NO3
|
|---|---|
| Molecular Weight |
131.13
|
| Exact Mass |
131.058
|
| CAS # |
3398-22-9
|
| PubChem CID |
440074
|
| Appearance |
White to off-white solid powder
|
| Density |
1.4±0.1 g/cm3
|
| Boiling Point |
355.2±42.0 °C at 760 mmHg
|
| Melting Point |
260°C
|
| Flash Point |
168.6±27.9 °C
|
| Vapour Pressure |
0.0±1.8 mmHg at 25°C
|
| Index of Refraction |
1.54
|
| LogP |
-1.84
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
9
|
| Complexity |
125
|
| Defined Atom Stereocenter Count |
2
|
| SMILES |
O([H])[C@]1([H])C([H])([H])N([H])[C@@]([H])(C(=O)O[H])C1([H])[H]
|
| InChi Key |
PMMYEEVYMWASQN-IUYQGCFVSA-N
|
| InChi Code |
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
|
| Chemical Name |
(2R,4S)-4-hydroxypyrrolidine-2-carboxylic acid
|
| Synonyms |
trans-D-4-Hydroxyproline
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.6260 mL | 38.1301 mL | 76.2602 mL | |
| 5 mM | 1.5252 mL | 7.6260 mL | 15.2520 mL | |
| 10 mM | 0.7626 mL | 3.8130 mL | 7.6260 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
