135837-63-7

Basic information

• Product Name: FMOC-3,4-DEHYDRO-PRO-OH
• Synonyms: FMOC-PRO(3,4-DEHYDRO)-OH;FMOC-DELTA-PRO-OH;FMOC-3,4-DEHYDRO-L-PROLINE;FMOC-3,4-DEHYDRO-L-PRO-OH;FMOC-3,4-DEHYDRO-PROLINE;FMOC-3,4-DEHYDRO-PRO-OH;(S)-1-FLUORENYLMETHOXYCARBONYL-2,5-DIHYDROPYRROLE-2-CARBOXYLIC ACID;N-FMOC-3,4-DEHYDRO-L-PROLINE
• CAS NO: 135837-63-7
• Molecular Formula: C₂₀H₁₇NO₄
• Molecular Weight: 335.35
• Product Categories: Amino Acid Derivatives;Amino Acids
• Mol File: 135837-63-7.mol

Chemical Properties

• Boiling Point: 549.6±50.0 °C(Predicted)
• Appearance: /
• Density: 1.356±0.06 g/cm3(Predicted)
• Storage Temp.: -15°C
• PKA: 3?+-.0.20(Predicted)
• CAS DataBase Reference: FMOC-3,4-DEHYDRO-PRO-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-3,4-DEHYDRO-PRO-OH(135837-63-7)
• EPA Substance Registry System: FMOC-3,4-DEHYDRO-PRO-OH(135837-63-7)

Safety Data

• WGK Germany: WGK 2 water endangering
• HazardClass: IRRITANT
• Hazardous Substances Data: 135837-63-7(Hazardous Substances Data)

Usage

Chemical Properties

White or off-white powder

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 4043-88-3 3,4-dehydro-L-proline 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 83548-49-6 (2S,4S)-2-methyl 1-tert-butyl 4-iodopyrrolidine-1,2-dicarboxylate 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 51154-06-4 (S)-2,5-dihydropyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 
• 74844-93-2 N-BOC-3,4-didehydro-(S)-proline methyl ester 

Downstream Products

• 1440521-90-3 C₃₉H₆₄N₁₂O₈ 

Relevant articles and documents

Epoxide derivatives of pipecolic acid and proline are inhibitors of pipecolate oxidase

The cis-4,5-epoxide derivative of L-pipecolic acid (2S,4S,5R-epoxypipecolic acid, cis-3) was synthesized and found to serve as an excellent substrate for L-pipecolate oxidase (L-PO) and also to cause time-dependent, irreversible inactivation of the enzyme. Data are presented showing this compound is a mechanism-based inhibitor of L-PO, whereas 2S,3R,4S-epoxyproline acts as a reversible inhibitor.

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.

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