trans-L-3-Hydroxyproline

Base Information

• Chemical Name: trans-L-3-Hydroxyproline
• CAS No.: 4298-08-2
• Molecular Formula: C5H9NO3
• Molecular Weight: 131.131
• Hs Code.: 29339980
• Mol file: 4298-08-2.mol

Synonyms:trans-L-3-Hydroxyproline;L-threo-3-hydroxyproline;3-trans-hydroxy-L-proline;CHEBI:57938;trans-3-hydroxy-L-proline zwitterion;(2S,3S)-3-hydroxypyrrolidinium-2-carboxylate

Chemical Property of trans-L-3-Hydroxyproline

Chemical Property:

• Appearance/Colour: White to light beige powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 235oC
• Refractive Index: 1.54
• Boiling Point: 355.233 °C at 760 mmHg
• PKA: 2.03±0.40(Predicted)
• Flash Point: 168.639 °C
• PSA: 69.56000
• Density: 1.395g/cm³
• LogP: -0.87740
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: -2.5
• 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%, ^*data from raw suppliers

trans-3-Hydroxy-L-proline ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C[NH2+]C(C1O)C(=O)[O-]
• Isomeric SMILES: C1C[NH2+][C@@H]([C@H]1O)C(=O)[O-]
• General Description: **L-Proline, 3-hydroxy-,(3S)-**, also known as trans-3-Hydroxy-L-proline, is a stereospecific hydroxyproline derivative used as a precursor in the synthesis of modified oligonucleotides. It serves as the starting material for producing 3-hydroxy-N-acetylprolinol derivatives, which are incorporated into oligonucleotides to enhance hybridization properties. These modifications enable interactions with complementary DNA/RNA and facilitate the formation of non-natural complexes, though with reduced stability compared to 4-hydroxyprolinol-based systems. L-Proline, 3-hydroxy-,(3S)-’s (2S,3S) configuration is critical for its role in broadening pairing interactions in synthetic nucleic acid applications.

Technology Process of trans-L-3-Hydroxyproline

There total 61 articles about trans-L-3-Hydroxyproline 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) → (2S,3R)-3-hydroxyproline (567-35-1,567-36-2,4298-05-9,4298-06-0,4298-08-2,14916-76-8,62182-84-7,104069-26-3,118492-86-7,119677-21-3)

Guidance literature:

With ferrous(II) sulfate heptahydrate; cis-3-proline hydroxylase type II; sodium L-ascorbate; at 37 ℃; for 16h; stereospecific reaction;

DOI:10.3762/bjoc.7.193

Reference yield: 98.0%

(2S,3R)-N-(benzyloxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid (1262015-07-5) → (2S,3R)-3-hydroxyproline (567-35-1,567-36-2,4298-05-9,4298-06-0,4298-08-2,14916-76-8,62182-84-7,104069-26-3,118492-86-7,119677-21-3)

Guidance literature:

With hydrogen; palladium(II) hydroxide; In methanol; at 25 ℃; for 12h; under 4137.29 Torr;

DOI:10.1016/j.tetlet.2010.10.086

Reference yield: 90.0%

(2S,3R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)pyrrolidine-2-carboxylic acid (166383-67-1) → (2S,3R)-3-hydroxyproline (567-35-1,567-36-2,4298-05-9,4298-06-0,4298-08-2,14916-76-8,62182-84-7,104069-26-3,118492-86-7,119677-21-3)

Guidance literature:

(2S,3R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)pyrrolidine-2-carboxylic acid; With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 2h;

With methyloxirane; In methanol; at 20 ℃; for 2h;

upstream raw materials:

cis-(3R)-(tert-butyldimethylsilyloxy)-2-cyano-1-methoxycarbonyl-3-pyrrolidine

(2S,3R)-tert-butyl 3-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

(2S,3R)-1-[(tert-butoxy)carbonyl]-3-hydroxypyrrolidine-2-carboxylic acid

(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidine-2-carboxylic acid

Downstream raw materials:

(2S,3R)-1-[(tert-butoxy)carbonyl]-3-hydroxypyrrolidine-2-carboxylic acid

Δ¹-pyrroline-5-carboxylic acid

(2S,3S,4R)-3,4-dihydroxy-L-proline

(2S,3R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-3-(prop-2-yn-1-yloxy)pyrrolidine-2-carboxylic acid

Refernces

Oligonucleotides with 3-hydroxy-N-acetylprolinol as sugar substitute

10.1016/S0040-4020(97)01047-8

The research investigates the synthesis and properties of oligonucleotides modified with 3-hydroxy-N-acetylprolinol as a sugar substitute. The purpose of the study is to develop oligonucleotides with improved hybridization efficiency for potential applications in antisense therapeutics. The researchers synthesized fully modified oligonucleotides using 3-O-phosphoramidites of monomethoxytritylated trans-3-hydroxy-N-[(N6-benzoyladenin-9-yl)-acetyl]-prolinol and trans-3-hydroxy-N-[(thymin-l-yl)-acetyl]-prolinol. Trans-3-Hydroxyproline was used as the starting material for the synthesis of 3-hydroxy-N-acetylprolinol derivatives. They found that the modified all-adenine oligonucleotides could hybridize with complementary DNA and RNA, while the all-thymine oligonucleotides did not interact with natural nucleic acids but could form triple-stranded complexes with modified strands of the same chirality. The study concludes that the 3-hydroxy-N-acetylprolinol system allows for broadened pairing interactions, including with both L and D compounds, and the formation of various homo-complexes, although the stability of these complexes is lower than those formed with 4-hydroxyprolinol oligonucleotides.