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L-Hydroxyproline CAS 51-35-4

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  • Appearance: White powder
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: L-Hydroxyproline Supplement

Basic Info of L-Hydroxyproline

What is L-Hydroxyproline?

Hydroxyproline is a non-essential amino acid divided from another amino acid called proline. It is created by the communication of proline with ascorbic acid vitamin C. This process produces a hydroxyl team bound to a hydrogen-oxygen particle, which is affixed to a carbon particle of proline as well as converted to hydroxyproline.Trans-4-hydroxy-l-proline is an optically energetic form of 4-hydroxyproline with l-trans setup. It can be used as human metabolite, plant metabolite and also computer mouse metabolite. It is an tautomer of trans-4-hydroxy-l-proline zwitterions.

Hydroxyproline is one of the 22 amino acids called for to compose human protein and also belongs to the common human hereditary code. Hydroxyproline is created in the intestinal system. Hydroxyproline can not be generated without vitamin C. Without it, it can also trigger severe issues because the body additionally can not produce collagen, the most essential protein framework. Both proline as well as hydroxyproline are very important for the development of this crucial compound, and also an absence of either can cause serious instability of collagen in the body.

L-Hydroxyproline is a typical non-standard protein amino acid, which has high application value as the primary resources of the antiviral medication atazanavir. L-Hydroxyproline is usually made use of as a food additive (made use of as a sweetener with a fairly percentage), as well as a reasonably huge quantity of intermediates utilized as penem side chains in medication.

L-Hydroxyproline Uses

  1. L-Hydroxyproline is produced by hydroxylation of amino acid proline by prolyl hydroxylase after protein synthesis (as post-translational alteration). Although it is not straight incorporated right into protein, hydroxyproline make up about 4% of all amino acids found in animal cells, and also its amount is higher than that of the various other 7 translation integrated amino acids.
  2. Flavour Enhancer; Nutritional Enhancer. fragrance. Mainly made use of for fruit juices, revitalizing beverages, nutritional beverages, etc as biochemical reagent.
  3. The most fundamental cause of scurvy is a lack of vitamin C, but it is manifested through a lack of collagen, which is directly related to insufficient hydroxyproline secretion. Without it, human collagen becomes unstable and excreted in urine. A lack of collagen can lead to easy bruising of the skin, damage to connective tissue, and the potential for internal bleeding. Additionally, a lack of this amino acid can cause hair loss and gum recession.
  4. The body does not cause deformities during stress and movement. But a lack of hydroxyproline can also cause this protein deficiency, but not as quickly or dramatically as collagen.
  5. Hydroxyproline is a neutral heterocyclic protein amino acid. It is present in collagen and is as a result common in many gelatin items. Hydroxyproline is mainly utilized as a diagnostic marker for bone turnover and also liver fibrosis. In terms of therapy, hydroxyproline is being examined as an experimental medication, but it has actually been accepted in France as a mixed local gel product called ciccative to treat little and also shallow injuries.

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Application of L-Hydroxyproline

Preparation of L-Hydroxyproline

A preparation method of L-hydroxyproline, specifically comprising the steps:

L-Hydroxyproline
  1. Add 100 g of pyroglutamic acid alcohol, 16.5 g of p-toluenesulfonic acid monohydrate, 130 g of benzaldehyde, and 350 g of toluene into a 2L reaction flask in turn, heat it to 70-120 °C for 4-6 hours, and evaporate under reduced pressure to evaporate the solvent toluene. The obtained oil was purified by column chromatography to obtain 40.5g of TSSA0200-A, HPLC: 95%, yield 23%;
  2. Take 30g of TSSA0200-A, add 900ml of tetrahydrofuran, add 90g of MoOPH to a 2L reaction flask, under nitrogen protection, warm to -40~-50℃, add 240g of LiHMDS dropwise, react for 6~10h, quench the reaction, and obtain 9.7 by column chromatography g TSSA0200-B, HPLC: 94.2%, yield: 30%;
  3. Add 5g of TSSA0200-B into a 100ml three-necked flask, add 50ml of tetrahydrofuran under nitrogen protection, cool down to -15~-20°C, add 0.8g of tetrahydroaluminum lithium, warm up to room temperature and react for 6~8h, quench the reaction, and perform column chromatography 1.5g of TSSA0200-C was obtained, HPLC: 97%, yield: 31.7%;
  4. Dissolve 1.5 g of TSSA0200-C with 30 ml of ethanol, add it to an autoclave, add 0.015 g of palladium carbon, pass hydrogen to 1 MPa, react for 3 h, and remove the palladium carbon by filtration to obtain 0.82 g of TSSA0200-D, yield: 96.5%;
  5. 0.082g of TEMPO was prepared into a 20wt% solution, 0.82g of TSSA0200-D was prepared into a 10wt% solution, pumped into a silica gel column to react for 5-10min to obtain a solution of TSSA0200-D, and 0.6g L- Hydroxyproline, yield 65.4%.

Reference

  1. L-Hydroxyproline – PubChem
  2. Gorres, Kelly L.; Raines, Ronald T. (April 2010). “Prolyl 4-hydroxylase”Critical Reviews in Biochemistry and Molecular Biology.
  3. [Chinese invention, Chinese invention authorization] CN201510895948.2 A preparation method of L-hydroxyproline [public]/a preparation method of L-hydroxyproline [authorization]

Quality Control of L-Hydroxyproline

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