296774-32-8

Basic information

• Product Name: FMOC-(2S,3S)-3-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
• Synonyms: N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-TRANS-3-HYDROXY-L-PROLINE;N-ALPHA-FMOC-L-TRANS-3-HYDROXYPROLINE;FMOC-HYP(3)-OH;FMOC-TRANS-3-HYDROXY-L-PROLINE;FMOC-TRANS-3-HYP-OH;FMOC-PRO(3-HYDROXY)-OH;FMOC-(2S,3S)-3-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID;(3S)-1-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-hydroxy-L-proline
• CAS NO: 296774-32-8
• Molecular Formula: C₂₀H₁₉NO₅
• Molecular Weight: 353.37
• Mol File: 296774-32-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: FMOC-(2S,3S)-3-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-(2S,3S)-3-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID(296774-32-8)
• EPA Substance Registry System: FMOC-(2S,3S)-3-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID(296774-32-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 296774-32-8(Hazardous Substances Data)

Usage

General Description

FMOC-(2S,3S)-3-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID is a chemical compound containing a fluorenylmethyloxycarbonyl (FMOC) protecting group and a (2S,3S)-3-hydroxypyrrolidine-2-carboxylic acid moiety. It is commonly used in organic synthesis as a building block for the preparation of various pharmaceuticals, peptides, and other biologically active molecules. The FMOC group serves as a protecting group that can be removed under mild conditions, allowing for selective manipulation of the compound's reactivity. The 3-hydroxypyrrolidine-2-carboxylic acid moiety has potential biological activity and can be used to modulate the properties of peptides and other biomolecules. Overall, FMOC-(2S,3S)-3-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID is a versatile and important compound in the field of chemical and pharmaceutical research.

Upstream product

• 147-85-3 L-proline 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 4298-08-2 trans-3-hydroxy-L-proline 

Downstream Products

• 166047-90-1 (2R,3S)-N-[(9-fluorenylmethoxy)carbonyl]-3-hydroxy-2-(hydroxymethyl)pyrrolidine 
• 325771-85-5 N-(9-fluorenylmethoxycarbonyl)-(2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-(dimethoxytrityl-hydroxymethyl)-pyrrolidine 
• 325771-86-6 N-(9-fluorenylmethoxycarbonyl)-(2R)-(2,4-dioxo-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-(dimethoxytrityl-hydroxymethyl)-pyrrolidine 
• 325771-77-5 N-(benzyloxycarbonyl)-(2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-4-(tert-butyldimethylsilyloxy)-(5R)-(tert-butyldimethylsilyloxymethyl)-aza-3-cyclopenten 
• 325771-72-0 N-(benzyloxycarbonyl)-(2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-hydroxymethyl-pyrrolidine 
• 325771-78-6 N-(benzyloxycarbonyl)-(2R)-(2,4-dioxo-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-hydroxymethyl-pyrrolidine 
• 325771-73-1 N-(benzyloxycarbonyl)-(4S)-(tert-butyldimethylsilyloxy)-(5R)-(tert-butyldimethylsilyloxymethyl)-aza-2-cyclopenten 
• 954127-74-3 fluoren-9-ylmethyl 5-[bis(4-methoxyphenyl)(phenyl)methoxymethyl]-4-hydroxy-2-[2-(2-phenoxyacetylamino)pyridin-5-yl]pyrrolidine-1-carboxylate 
• 954127-73-2 fluoren-9-ylmethyl 4-hydroxy-5-(hydroxymethyl)-2-[2-(2-phenoxyacetylamino)pyridin-5-yl]pyrrolidine-1-carboxylate 
• 954127-72-1 fluoren-9-ylmethyl 4-(tert-butyldimethylsilanyloxy)-5-(tert-butyldimethylsilanyloxymethyl)-2-[2-(2-phenoxyacetylamino)pyridin-5-yl]pyrrolidine-1-carboxylate 
• 954127-68-5 fluoren-9-ylmethyl 5-[bis(4-methoxyphenyl)(phenyl)methoxymethyl]-4-hydroxy-2-{2-[2-(4-nitrophenyl)ethoxy]pyridin-2-yl}pyrrolidine-1-carboxylate 
• 954127-67-4 fluoren-9-ylmethyl 4-hydroxy-5-(hydroxymethyl)-2-{2-[2-(4-nitrophenyl)ethoxy]pyridin-2-yl}pyrrolidine-1-carboxylate 
• 954127-66-3 fluoren-9-ylmethyl 4-(tert-butyldimethylsilanyloxy)-5-(tert-butyldimethylsilanyloxymethyl)-2-{2-[2-(4-nitrophenyl)ethoxy]pyridin-2-yl}pyrrolidine-1-carboxylate 
• 443899-48-7 (+)-(2S,3R)-3-tert-butoxy-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 

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.

Pyrrolidino DNA with bases corresponding to the 2-oxo deletion mutants of thymine and cytosine: Synthesis and triplex-forming properties

The dual recognition properties of pyrrolidino DNA species as parallel triplex-forming oligonucleotides were previously found to be strongly dependent upon the nature of the pyrimidine bases. In the structure-activity study presented here we were able to

BIOLOGICALLY ACTIVE COMPOUNDS

Compounds of general formula (I) wherein: Z = CR3R4, where R3 and R4 are independently chosen from CO-7-alkyl P1 = CR5R6, P2 = O, CR7R8/sup