ChemicalBook CAS DataBase List L-Hydroxyproline

L-Hydroxyproline synthesis

9synthesis methods

Product Name:L-Hydroxyproline
CAS Number:51-35-4
Molecular formula:C5H9NO3
Molecular Weight:131.13

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.

147-85-3 Synthesis

147-85-3
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$6.00/25g

51-35-4
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$6.00/5g

Yield:51-35-4 > 95 %Chromat.

Reaction Conditions:

with hydrogenchloride;α-ketoglutaric acid;ammonium iron (II) sulfate;L-proline trans-4-hydroxylase;sodium L-ascorbate in aq. buffer at 21; pH=6.5; for 14 h;Enzymatic reaction;

Steps:

1.4.5.1. LC/MS Assays

General procedure: Analytical scale proline hydroxylase (PH) incubations were performed by sequential addition of the reagents in Table S1 to a 1.5 mL Eppendorf tube (100 μL final volume): The incubation mixture was kept at 21 °C for 14 h (unless otherwise stated). To quench the reaction, an equal volume of methanol was added and the mixture cooled on ice for 10 min before centrifugation (13,000g for 3 min); the quenching methanol contained 0.25 mM p-aminosalicylic acid (pASA) as an internal standard. The supernatant was decanted and analysed by an LC/MS. ‘Negative controls’ were performed in parallel, but with substitution of 50 mM MES-NaOH, pH 6.5 for the enzyme solution.

References:

Smart, Tristan J.;Hamed, Refaat B.;Claridge, Timothy D.W.;Schofield, Christopher J. [Bioorganic Chemistry,2020,vol. 94,art. no. 103386] Location in patent:supporting information

90600-20-7 Synthesis