14916-76-8

Basic information

• Product Name: L-Proline, 3-hydroxy-
• CAS NO: 14916-76-8
• Molecular Formula: C5H9NO3
• Molecular Weight: 131.131
• Mol File: 14916-76-8.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: L-Proline, 3-hydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline, 3-hydroxy-(14916-76-8)
• EPA Substance Registry System: L-Proline, 3-hydroxy-(14916-76-8)

Safety Data

• Hazardous Substances Data: 14916-76-8(Hazardous Substances Data)

Upstream product

• 186132-96-7 (2S,3R)-1-[(tert-butoxy)carbonyl]-3-hydroxypyrrolidine-2-carboxylic acid 
• 125787-20-4 cis-(3R)-(tert-butyldimethylsilyloxy)-2-cyano-1-methoxycarbonyl-3-pyrrolidine 
• 147-85-3 L-proline 
• 166383-67-1 (2S,3R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)pyrrolidine-2-carboxylic acid 
• 1262015-07-5 (2S,3R)-N-(benzyloxycarbonyl)-3-hydroxypyrrolidine-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 
• 166383-69-3 (2R,3R)-1-t-Butoxycarbonyl-2-benzyloxymethyl-3-hydroxypyrrolidine 
• 166383-82-0 (2R,3R)-2-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 174541-85-6 (4R,5R)-4-Benzyloxymethyl-5-(2-chloro-ethyl)-oxazolidin-2-one 
• 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

• 95341-65-4 (2S,3S,4R)-3,4-dihydroxy-L-proline 
• 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 
• 1432734-10-5 (2S,3R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-3-(prop-2-yn-1-yloxy)pyrrolidine-2-carboxylic acid 
• 64199-88-8 Δ¹-pyrroline-5-carboxylic acid 
• 186132-96-7 (2S,3R)-1-[(tert-butoxy)carbonyl]-3-hydroxypyrrolidine-2-carboxylic acid 
• 496841-04-4 methyl (2S,3S)-3-hydroxypyrrolidine-2-carboxylate 
• 187039-57-2 (2S,3S)-1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid 

Relevant articles and documents

Discovery of New Fe(II)/α-Ketoglutarate-Dependent Dioxygenases for Oxidation of l-Proline

Genome mining for novel Fe(II)/α-ketoglutarate-dependent dioxygenases (αKGDs) to expand the enzymatic repertoire in the oxidation of l-proline is reported. Through clustering of proteins, we predicted regio- and stereoselectivity in the hydroxylation reaction and validated this hypothesis experimentally. Two novel byproducts in the reactions with enzymes from Bacillus cereus and Streptomyces sp. were isolated, and the structures were determined to be a 3,4-epoxide and a 3,4-diol, respectively. The mechanism for the formation of the epoxide was investigated by performing an 18O-labeling experiment. We propose that the mechanism proceeds via initial cis-3-hydroxylation followed by ring closure. A biocatalytic step was run on subgram quantities of starting material without any significant optimization of the conditions. However, the substrate concentration was 40-fold higher than the usual reported titers for recombinant P450-mediated hydroxylations, showing the synthetic potential of αKGDs on a preparative scale.

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.