88050-17-3

Basic information

• Product Name: Fmoc-L-hydroxyproline
• Synonyms: RARECHEM EM WB 0137;N-FMOC-TRANS-4-HYDROXY-L-PROLINE;N-FMOC-L-TRANS-4-HYDROXYPROLINE;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-TRANS-L-HYDROXYPROLINE;N-ALPHA-FMOC-L-TRANS-4-HYDROXYPROLINE;(2S,4R)-N-ALPHA-(Y-FLUORENYLMETHOXYCARBONYL)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID;(2S,4R)-N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID;FMOC-(2S,4R)-(-)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
• CAS NO: 88050-17-3
• Molecular Formula: C₂₀H₁₉NO₅
• Molecular Weight: 353.37
• EINECS: 1533716-785-6
• Product Categories: Heterocyclic Compounds;Amino Acids;Hydroxyproline [Hyp];Unusual Amino Acids;Fmoc-Amino acid series
• Mol File: 88050-17-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 189-193 °C
• Boiling Point: 595.5 °C at 760 mmHg
• Flash Point: 314 °C
• Appearance: /
• Density: 1.407 g/cm³
• Vapor Pressure: 4.98E-15mmHg at 25°C
• Refractive Index: 1.658
• Storage Temp.: 2-8°C
• PKA: 3.74±0.40(Predicted)
• BRN: 4574378
• CAS DataBase Reference: Fmoc-L-hydroxyproline(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-L-hydroxyproline(88050-17-3)
• EPA Substance Registry System: Fmoc-L-hydroxyproline(88050-17-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 88050-17-3(Hazardous Substances Data)

Usage

Chemical Properties

Light brown solid

InChI:InChI=1/C20H19NO5/c22-12-9-18(19(23)24)21(10-12)20(25)26-11-17-15-7-3-1-5-13(15)14-6-2-4-8-16(14)17/h1-8,12,17-18,22H,9-11H2,(H,23,24)/t12-,18+/m1/s1

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 147-85-3 L-proline 

Downstream Products

• 748142-27-0 (3S,7R,8aS)-7-hydroxy-3-methylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 178113-42-3 (9H-fluoren-9-yl)methyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 1325728-16-2 C₄₃H₃₅NO₆ 
• 1325728-20-8 C₄₆H₃₈N₂O₇ 
• 1325728-22-0 C₄₆H₄₀N₂O₇ 
• 1325728-26-4 C₅₅H₅₆N₂O₇ 
• 1325728-27-5 C₅₅H₅₈N₂O₇ 
• 1325728-14-0 C₄₃H₃₃NO₆ 
• 1616889-82-7 chlorambucil-Gln-Hyp-Arg-Lys-(Py)4-Lys-Arg-NH₂ 
• 1616889-81-6 chlorambucil-Met-Hyp-Arg-Lys-(Py)4-Lys-Arg-NH₂ 
• 187223-15-0 Fmoc-(2S,4R)-(4-OCO-NH-CH₂-CH₂-NH-Boc)-Pro-OH 

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.