118492-86-7

Basic information

• Product Name: (+)-CIS-(2R,3S)-3-Hydroxyproline
• Synonyms: (+)-CIS-(2R,3S)-3-Hydroxyproline;D-Leucine, 3-hydroxy-,(3S)-;cis-3-Hydroxy-D-proline;(2R,3S)-3-hydroxypyrrolidine-2-carboxylic acid;(3S)-3-Hydroxy-D-proline
• CAS NO: 118492-86-7
• Molecular Formula: C₅H₉NO₃
• Molecular Weight: 131.12986
• EINECS: -0
• Mol File: 118492-86-7.mol
• Article Data: 20

Chemical Properties

• Melting Point: 240-255℃ (dec.)
• Boiling Point: 355.2±42.0 °C(Predicted)
• Appearance: /
• Density: 1.395±0.06 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: 2-8°C
• PKA: 2.03±0.40(Predicted)
• CAS DataBase Reference: (+)-CIS-(2R,3S)-3-Hydroxyproline(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-CIS-(2R,3S)-3-Hydroxyproline(118492-86-7)
• EPA Substance Registry System: (+)-CIS-(2R,3S)-3-Hydroxyproline(118492-86-7)

Safety Data

• Hazardous Substances Data: 118492-86-7(Hazardous Substances Data)

Usage

General Description

(+)-CIS-(2R,3S)-3-Hydroxyproline, also known as trans-4-Hydroxy-L-proline, is a naturally occurring, non-proteinogenic amino acid that is commonly found in collagen and other connective tissues in the human body. It is a chiral molecule with two stereocenters, and it exists in the L-configuration, with the 4-hydroxy group in the trans orientation. (+)-CIS-(2R,3S)-3-Hydroxyproline is important for the stability and structure of collagen, as it can form stable intramolecular hydrogen bonds to help stabilize the collagen triple helix structure. In addition, (+)-CIS-(2R,3S)-3-Hydroxyproline has been found to have potential therapeutic and pharmaceutical applications, including wound healing and tissue regeneration. It is also being studied for its potential role in developing new biomaterials and drug delivery systems.

Upstream product

• 123287-88-7 (2S,3R)-tert-butyl 3-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 147-85-3 L-proline 
• 174541-85-6 (4R,5R)-4-Benzyloxymethyl-5-(2-chloro-ethyl)-oxazolidin-2-one 
• 166383-82-0 (2R,3R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 166383-69-3 (2R,3R)-1-t-Butoxycarbonyl-2-benzyloxymethyl-3-hydroxypyrrolidine 
• 1262015-07-5 (2S,3R)-N-(benzyloxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid 
• 174389-11-8 (2R,3S)-N-(benzyloxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid 
• 166383-67-1 (2S,3R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)pyrrolidine-2-carboxylic acid 
• 174541-86-7 (2R,3R)-1-benzyloxy-2-(tert-butoxycarbonyl)amino-3,5-pentandiol 
• 186132-95-6 2-benzyl 1-(tert-butyl)(2S,3R)-3-hydroxypyrrolidine-1,2-dicarboxylate 
• 87125-48-2 cis-N-(tert-butoxycarbonyl)-3-hydroxy-DL-proline 
• 153805-41-5 methyl (4R,5R)-4-(benzyloxy)methyl-2-oxo-5-oxazolidineacetate 
• 153805-45-9 (4R,5R)-4-(benzyloxy)methyl-5-(2-hydroxyethyl)-2-oxo-oxazolidine 
• 161161-54-2 GR₁₂₂₂₂₂X 

Downstream Products

• 118492-87-8 (3S)-1-(tert-butoxycarbonyl)-3-hydroxy-D-proline 
• 95341-65-4 (2S,3S,4R)-3,4-dihydroxy-L-proline 
• 1432734-10-5 (2S,3R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-3-(prop-2-yn-1-yloxy)pyrrolidine-2-carboxylic acid 
• 654083-19-9 3,4-dihydroxy-l-proline 
• 496841-08-8 cis-3-hydroxy-L-proline methyl ester 
• 130966-46-0 (2S,3R)-N-tert-Butyloxycarbonyl-3-hydroxy-2-pyrrolidinecarboxylic Acid Methyl Ester 
• 64199-88-8 Δ¹-pyrroline-5-carboxylic acid 
• 186132-96-7 (2S,3R)-1-[(tert-butoxy)carbonyl]-3-hydroxypyrrolidine-2-carboxylic acid 

Relevant articles and documents

Modular Chemoenzymatic Synthesis of GE81112 B1 and Related Analogues Enables Elucidation of Its Key Pharmacophores

The GE81112 complex has garnered much interest due to its broad antimicrobial properties and unique ability to inhibit bacterial translation initiation. Herein we report the use of a chemoenzymatic strategy to complete the first total synthesis of GE81112 B1. By pairing iron and α-ketoglutarate dependent hydroxylases found in GE81112 biosynthesis with traditional synthetic methodology, we were able to access the natural product in 11 steps (longest linear sequence). Following this strategy, 10 GE81112 B1 analogues were synthesized, allowing for identification of its key pharmacophores. A key feature of our medicinal chemistry effort is the incorporation of additional biocatalytic hydroxylations in modular analogue synthesis to rapidly enable exploration of relevant chemical space.

Studies on the selectivity of proline hydroxylases reveal new substrates including bicycles

Studies on the substrate selectivity of recombinant ferrous-iron- and 2-oxoglutarate-dependent proline hydroxylases (PHs) reveal that they can catalyse the production of dihydroxylated 5-, 6-, and 7-membered ring products, and can accept bicyclic substrates. Ring-substituted substrate analogues (such hydroxylated and fluorinated prolines) are accepted in some cases. The results highlight the considerable, as yet largely untapped, potential for amino acid hydroxylases and other 2OG oxygenases in biocatalysis.

Regio- and stereoselective oxygenation of proline derivatives by using microbial 2-oxoglutarate-dependent dioxygenases

We evaluated the substrate specificities of four proline cis-selective hydroxylases toward the efficient synthesis of proline derivatives. In an initial evaluation, 15 proline-related compounds were investigated as substrates. In addition to L-proline and L-pipecolinic acid, we found that 3,4-dehydro-L-proline, L-azetidine-2-carboxylic acid, cis-3-hydroxy-L-proline, and L-thioproline were also oxygenated. Subsequently, the product structures were determined, revealing cis-3,4-epoxy-L-proline, cis-3-hydroxy-L-azetidine-2-carboxylic acid, and 2,3-cis-3,4-cis-3,4-dihydroxy-L-proline.