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

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

Uses

Used in Pharmaceutical Synthesis:
FMOC-(2S,3S)-3-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID is utilized as a key building block in the synthesis of various pharmaceuticals. Its presence allows for the creation of complex molecular structures that can be tailored for specific therapeutic applications.
Used in Peptide Synthesis:
In the field of peptide synthesis, FMOC-(2S,3S)-3-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID is employed as a component that contributes to the formation of peptide sequences. The FMOC group ensures that the compound can be selectively incorporated and later removed, providing a high degree of control over the synthesis process.
Used in Organic Synthesis:
FMOC-(2S,3S)-3-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID is also used in organic synthesis as a versatile intermediate. Its ability to be selectively protected and deprotected makes it an ideal candidate for the construction of intricate organic molecules.
Used in Research and Development:
In research and development, FMOC-(2S,3S)-3-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID is applied as a valuable tool for studying the properties and interactions of biomolecules. Its potential biological activity and the ability to manipulate its reactivity make it a useful probe in various biological assays and experiments.
Used in Drug Design:
FMOC-(2S,3S)-3-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID is used in drug design to create novel therapeutic agents. Its incorporation into drug candidates can enhance their efficacy, selectivity, and pharmacokinetic properties, leading to the development of more effective treatments for a range of diseases.
Used in Chemical Modification of Biomolecules:
In the modification of biomolecules, FMOC-(2S,3S)-3-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID is employed as a chemical entity that can be attached to peptides, proteins, and other biological molecules. This modification can alter their function, stability, or interactions with other molecules, providing new insights into their mechanisms of action and potential applications.

Upstream product

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

Downstream Products

• 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 
• 443899-48-7 (+)-(2S,3R)-3-tert-butoxy-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 
• 266359-42-6 (-)-(2S,3S)-3-tert-butoxy-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 
• 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 

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.

Method for assaying OGFOD1 activity

The present invention relates to assays for monitoring activity of OGFOD1 activity, in particular, to assays for identifying modulators of OGFOD1 activity. The invention also relates to assays to monitor the prolyl hydroxylase activity of OGFOD1 on its substrate, the human ribosomal protein RPS23. The invention also enables the introduction of 3-hydroxyprolyl residues into peptides and proteins.

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

Bicyclic peptidomimetic tetrahydrofuro[3,2-b]pyrrol-3-one and hexahydrofuro[3,2-b]pyridine-3-one based scaffolds: Synthesis and cysteinyl proteinase inhibition

Fmoc protected 5,5 and 6,5-bicyclic ketones 12 and 13 were prepared through the corresponding diazomethylketone intermediates via a lithium chloride/acetic acid promoted carbene insertion reaction. Building blocks 12 and 13 were used in the solid phase synthesis of peptidomimetic inhibitors of a range of CAC1 cysteinyl proteinases. Compound 10, a potent and selective inhibitor of cathepsin K exhibited promising activity in an in vitro cell-based human osteoclast assay of bone resorption. A stereoselective synthesis of (3aS,6aR)-tetrahydrofuro[3,2-b]pyrrol-3-ones and (3aS,7aR)-hexahydrofuro[3,2-b] pyridine-3-ones has been developed through Fmoc protected scaffolds 12 and 13. A key design element within these novel bicyclic scaffolds, in particular the 5,5-fused system, was the inherent stability of the cis-fused geometry in comparison to that of the corresponding trans-fused. Since the bridgehead stereocentre situated α to the ketone was of a fixed and stable configuration, the fact that cis ring fusion is both kinetically and thermodynamically stable with respect to trans ring fusion provides chiral stability to the bridgehead stereocentre that is situated β to the ketone. To exemplify this principle, building blocks 12 and 13 were designed, prepared and utilised in a solid phase combinatorial synthesis of peptidomimetic inhibitors 10, 45a-e, 11 and 46. Both series were chirally stable with 5,5-series 10 and 45a-e exhibiting potent in vitro activity against a range of CAC1 cysteinyl proteinases. Compound 10, a potent and selective inhibitor of cathepsin K, possessed good primary DMPK properties along with promising activity in an in vitro cell-based human osteoclast assay of bone resorption.

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

Synthesis of pyrrolidine C-nucleosides via Heck reaction.

[figure: see text] A novel method for the synthesis of pyrrolidine C-nucleosides has been developed. The key step of the synthesis is the palladium(0)-mediated coupling of a disubstituted N-protected 2-pyrroline and 5-iodouracil. C-Nucleoside 14 and its N