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| | L-Hydroxyproline Basic information |
| | L-Hydroxyproline Chemical Properties |
| Melting point | 273 °C (dec.)(lit.) | | alpha | -75.5 º (c=5, H2O) | | Boiling point | 242.42°C (rough estimate) | | density | 1.3121 (rough estimate) | | vapor density | 4.5 (vs air) | | refractive index | -75.5 ° (C=4, H2O) | | storage temp. | Store below +30°C. | | solubility | H2O: 50 mg/mL | | form | Crystals or Crystalline Powder | | pka | 1.82, 9.66(at 25℃) | | color | White | | PH | 5.5-6.5 (50g/l, H2O, 20℃) | | Odor | Odorless | | optical activity | [α]25/D 75.6°, c = 1 in H2O | | Water Solubility | 357.8 g/L (20 º C) | | Merck | 14,4840 | | BRN | 471933 | | InChIKey | PMMYEEVYMWASQN-DMTCNVIQSA-N | | LogP | -0.350 (est) | | CAS DataBase Reference | 51-35-4(CAS DataBase Reference) | | NIST Chemistry Reference | Hydroxyproline(51-35-4) | | EPA Substance Registry System | trans-4-Hydroxy-L-proline (51-35-4) |
| | L-Hydroxyproline Usage And Synthesis |
| Description | A non-essential amino acid. Can be isolated from gelatin. Hydroxyproline has not been reported as added to food in any of the NAS
surveys.
| | Chemical Properties | White crystalline powder | | Uses | A natural constituent of animal structural proteins such as collagen and elastin. Several microorganisms producing proline trans-4- and cis-3-hydroxylase were discovered and these enzymes were applied
to the industrial production of trans-4- and cis-3-hydroxy-L-proline. | | Uses | A versatile reagent for the synthesis of neuroexcitatory kainoids and antifungal echinocandins. | | Uses | hydroxyproline is a skin-conditioning amino acid. It is a component of collagen. | | Definition | ChEBI: An optically active form of 4-hydroxyproline having L-trans-configuration. | | Production Methods | In the past L-Hydroxyproline was isolated by hydrolysis of animal collagen, e. g. gelatine or collagen, of which it is a major constituent. L-Hydroxyproline is an unnatural amino acid which is made in the body by hydroxylation of L-Proline. The presence of L-Hydroxyproline and proline are key to maintaining the stability of the tight collagen helix.
Today L-Hydroxyproline is manufactured by bio-catalysed hydroxylation of proline in bacteria. Together with its other isomers, L-Hydroxyproline is also used as an inter mediate for a range of pharmaceutical active ingredients.
Produced by hydroxylation of L-proline after protein synthesis. It is contained rich in collagen and elastin. Known to stabilization of triple-helix structure of collagen. Widely used as an intermediate for medicines. | | General Description | Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards | | Biochem/physiol Actions | 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. | | Purification Methods | Crystallise it from MeOH/EtOH (1:1). Separation from normal allo-isomer can be achieved by crystallisation of the copper salts [see Levine Biochemical Preparations 8 114 1961]. Separation from proline is achieved via the crystalline picrate, CdCl2, or acid ammonium rhodanate salts [see Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 p 2182 1961, Kapfhammer & Mohn Z Physiol Chem 306 76 1956]. [Beilstein 22/5 V 7.] |
| | L-Hydroxyproline Preparation Products And Raw materials |
| Raw materials | Α-PROTEIN-->Casein-->Gelatin-->Soy bean Isoflavone Isoflavone 10-40%-->Bone glue | | Preparation Products | (R)-(-)-3-Pyrrolidinol hydrochloride-->N-Boc-cis-4-Hydroxy-L-proline methyl ester-->(2S,4S)-(-)-N-BOC-4-Diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidine-->tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride-->BOC-4-OXO-PRO-OME-->Fmoc-L-hydroxyproline-->3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid-->1-Pyrrolidinecarboxylic acid, 2-(hydroxymethyl)-4-methyl-, 1,1-dimethylethyl ester, (2S,4S)--->2-PyrrolidineMethanol, 4-hydroxy-, hydrochloride (1:1), (2S,4R)--->BETONICINE-->TRANS-4-HYDROXY-1-(4-NITROBENZYLOXYCARBONYL)-L-PROLINE-->N-CBZ-CIS-4-HYDROXY-D-PROLINE METHYL ESTER-->1-BENZYLPYRROLE-->1-PHENYLPYRROLE |
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