(2S,4S)-4-hydroxypyrrolidinium-2-carboxylate

Base Information

• Chemical Name: (2S,4S)-4-hydroxypyrrolidinium-2-carboxylate
• CAS No.: 618-27-9
• Molecular Formula: C5H9NO3
• Molecular Weight: 131.131
• Hs Code.: 29339900
• Mol file: 618-27-9.mol

Synonyms:CIS-L-4-HYDROXYPROLINE;cis-oxyproline;cis-hydroxy-L-proline;cis-L-4-hydroxy-proline;CHEBI:63727;cis-4-hydroxy-L-proline zwitterion;(2S,4S)-4-hydroxypyrrolidinium-2-carboxylate

Chemical Property of (2S,4S)-4-hydroxypyrrolidinium-2-carboxylate

Chemical Property:

• Appearance/Colour: White to beige powder
• Melting Point: 257 ºC (dec.)(lit.)
• Refractive Index: -59 ° (C=2, H2O)
• Boiling Point: 355.2 ºC at 760 mmHg
• PKA: 2.14±0.40(Predicted)
• Flash Point: 168.6 ºC
• PSA: 69.56000
• Density: 1.395 g/cm³
• LogP: -0.87740
• Storage Temp.: Store at RT.
• Solubility.: soluble
• Water Solubility.: soluble
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 131.058243149
• Heavy Atom Count: 9
• Complexity: 120

Purity/Quality:

99.9% ^*data from raw suppliers

cis-4-Hydroxy-L-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(C[NH2+]C1C(=O)[O-])O
• Isomeric SMILES: C1[C@@H](C[NH2+][C@@H]1C(=O)[O-])O
• Uses: Hydroxyprolines are valuable chiral building blocks for organic synthesis of pharmaceuticals. 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. cis-4-Hydroxy-L-proline (CHP) is a proline analog that inhibits collagen synthesis and has been used as an anticancer compound. CHP blocked myotube formation and expression of sarcomeric myosin heavy chain in C2C12 murine skeletal muscle cells. CHP inhibited proliferation of murine Panc02 pancreatic carcinoma cell line3 and rat pancreatic carcinoma cell line DSL6A. cis-4-Hydroxy-L-proline and other hydrosyl-L-prolines are important intermediates for chiral synthesis of potential drugs. cis-4-Hydroxy-L-proline (CHP) is a proline analog that inhibits collagen synthesis and has been used as an anticancer compound. CHP blocked myotube formation and expression of sarcomeric myosin heavy chain in C2C12 murine skeletal muscle cells. CHP inhibited proliferation of murine Panc02 pancreatic carcinoma cell line and rat pancreatic carcinoma cell line DSL6A.

Technology Process of (2S,4S)-4-hydroxypyrrolidinium-2-carboxylate

There total 53 articles about (2S,4S)-4-hydroxypyrrolidinium-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → hydroxy L-proline (618-27-9,30724-02-8)

Guidance literature:

With ferrous(II) sulfate heptahydrate; cis-4-proline hydroxylase; sodium L-ascorbate; at 25 ℃; for 16h; stereospecific reaction;

DOI:10.3762/bjoc.7.193

Reference yield: 100.0%

(2S,4S)-4-Benzoyloxy-pyrrolidine-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (157401-62-2) → hydroxy L-proline (618-27-9,30724-02-8)

Guidance literature:

With hydrogenchloride; at 140 ℃; for 3h;

DOI:10.1039/C39940001291

Reference yield: 87.0%

(2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline (13504-86-4) → hydroxy L-proline (618-27-9,30724-02-8)

Guidance literature:

With hydrogenchloride; In water; at 80 ℃; for 1h;

upstream raw materials:

N-acetyl-cis-4-hydroxy-L-proline

cis-1-ethoxycarbonyl-4-hydroxy-L-proline

cis-4-hydroxy-N-triphenylmethyl-L-proline

(2S,4S)-4-hydroxy-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester)

Downstream raw materials:

cis-4-hydroxy-L-prolin-ethyl ester

cis-1-(2,4-dinitro-phenyl)-4-hydroxy-L-proline

(2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline

4-Hydroxy-1-propyl-pyrrolidine-2-carboxylic acid

Refernces

• 1、 Zwick, Christian R.,Sosa, Max B.,Renata, Hans. "Modular Chemoenzymatic Synthesis of GE81112 B1 and Related Analogues Enables Elucidation of Its Key Pharmacophores". supporting information. p. 1673 - 1679. Retrieved 2021/01/25.
• 2、 Smart, Tristan J.,Hamed, Refaat B.,Claridge, Timothy D.W.,Schofield, Christopher J.. "Studies on the selectivity of proline hydroxylases reveal new substrates including bicycles". supporting information. . Retrieved 2019/11/26.