159551-89-0

Basic information

• Product Name: (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid dibenzyl ester
• Synonyms: (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid dibenzyl ester
• CAS NO: 159551-89-0
• Molecular Weight: 337.375
• Mol File: 159551-89-0.mol

Chemical Properties

• CAS DataBase Reference: (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid dibenzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid dibenzyl ester(159551-89-0)
• EPA Substance Registry System: (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid dibenzyl ester(159551-89-0)

Safety Data

• Hazardous Substances Data: 159551-89-0(Hazardous Substances Data)

Upstream product

• 159551-88-9 dibenzyl (2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate 
• 13500-53-3 N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester 
• 501-53-1 benzyl chloroformate 
• 159551-87-8 (2S,4R)-N^α-Cbz-4-[(p-toluenesulfonyl)oxy]proline benzyl ester 
• 51-35-4 4R-4-hydroxyproline 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 100-39-0 benzyl bromide 
• 1426534-95-3 N-Cbz-trans-4-methylxanthate-L-proline 
• 1426534-96-4 N-Cbz-trans-4-methylxanthate-L-proline benzyl ester 
• 4043-88-3 3,4-dehydro-L-proline 
• 161813-74-7 (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-benzyl ester 

Downstream Products

• 159551-91-4 dibenzyl (2S,3R,4S)-3,4-dihydroxypyrrolidine-1,2-dicarboxylate 
• 159651-34-0 (1S,2S,5R)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid dibenzyl ester 
• 159551-90-3 (1R,2S,5S)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid dibenzyl ester 
• 202473-13-0 (2S,3RS,4SR)-N-benzyloxycarbonyl-3,4-dihydroxyproline benzyl ester 
• 202473-18-5 (2S,3S,4R)-3-hydroxy-4-aminoproline 
• 202473-18-5 (2S,3R,4S)-3-hydroxy-4-aminoproline 
• 654083-19-9 (2S,3RS,4SR)-3,4-dihydroxyproline 
• 202473-19-6 (2S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester 
• 202473-17-4 (2S,3R,4R)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester 
• 202473-20-9 (2S,3R,4R)-N-benzyloxycarbonyl-3-azido-4-hydroxyproline benzyl ester 
• 95341-64-3 (2S,3R,4S)-3,4-dihydroxypyrrolidine-2-carboxylic acid 
• 1386459-21-7 (2S,3R,4R)-3-hydroxy-4-methoxy-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester 
• 1426535-08-1 N-Cbz-cis-3-hydroxy-trans-4-isopropoxy-L-proline benzyl ester 
• 1426535-09-2 N-Cbz-trans-3-hydroxy-cis-4-benzyloxy-L-proline benzyl ester 

Relevant articles and documents

Scaling the Amphiphilic Character and Antimicrobial Activity of Gramicidin S by Dihydroxylation or Ketal Formation

The acid lability of aliphatic ketals, which often serve as protection groups for 1,2-diols, is influenced by their local structural environment. The acetonide of the protected amino acid cis-dihydroxyproline (Dyp) is a typical protecting group cleavable by traces of TFA. The tricyclic acetonide of the dipeptide d-Hot-Tap is resistant to TFA and thus can serve as a bioorthogonal modification of bioactive peptides. With the aim of improving antimicrobial activity and hemolytic properties, we use these reactivity differences to scale the membrane affinity of the decapeptide Gramicidin S cyclo(d-Phe-Pro-Val-Orn-Leu-)2 (GS). The cis-dihydroxylated amino acids are used to increase the polarity of GS or obversely decrease the polarity by stereoselective ketal formation with an aliphatic ketone. While Dyp (GS mimetic 15) has only minimal influence on the biological properties of GS, d-Hot-Tap at the position of d-Phe1-Pro2 eradicates the biological activity (GS mimetic 16). The acid-stable ketals 17-19 are bioorthogonal modifications which reconstitute the biological activity of GS. We describe an improved synthesis of orthogonally protected Fmoc-Dyp-acetonide (9) and of several Fmoc-d-Hot-Tap-ketals for solid-phase peptide synthesis.

PYRROLIDINE DERIVATIVES AND THEIR USE AS COMPLEMENT PATHWAY MODULATORS

The present invention provides a compound of formula (I) a method for manufacturing the compounds of the invention and its therapeutic uses as complement pathway modulators for the treatment of ocular diseases. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

PYRROLIDINE DERIVATIVES AND THEIR USE AS COMPLEMENT PATHWAY MODULATORS

The present invention provides a compound of formula I: (I) a method for manufacturing the compounds of the invention, and its therapeutic uses as complement alternative inhibitors for the treatment of ocular diseases. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

COMPLEMENT PATHWAY MODULATORS AND USES THEREOF

The present invention provides a compound of formula I: (I) a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

PYRROLIDINE DERIVATIVES AND THEIR USE AS COMPLEMENT PATHWAY MODULATORS

The present invention provides a compound of formula (I) a method for manufacturing the compounds of the invention, and its therapeutic uses as a factor D inhibitor for the treatment of ophthalmic diseases. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

COMPLEMENT PATHWAY MODULATORS AND USES THEREOF

The present invention provides a compound of formula I: a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

PYRROLIDINE DERIVATIVES AND THEIR USE AS COMPLEMENT PATHWAY MODULATORS

The present invention provides a compound of formula (I) a method for manufacturing the compounds of the invention, and its therapeutic uses as complement pathway modulators for the treatment of ocular diseases. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

Novel Inhibitors of the Amino Acid Transporters ASCT1 and ASCT2

The invention features compounds and methods relating to novel hydroxy-proline analog inhibitors of the ASCT1 and ASCT2 neutral amino acid transporters. These analogs are potent and selective inhibitors of ASCT2 and ASCT1-mediated amino acid transport as evidenced by significantly reduced glutamine or alanine transport-associated currents or radiolabeled substrate (amino acid) uptake in Xenopus oocytes expressing ASCT2 or ASCT1. Selectivity has been established in the same manner whereby reduced substrate associated current or substrate uptake is unobserved in Xenopus oocytes expressing ATA2, SN1, or EAAT(s) (excitatory amino acid transporter). The compounds and methods of the invention can be used in research or clinical applications (e.g., for the treatment of cancer, microbial infection, or ischemia-related central nervous system injury).

Synthesis of (2S, 3R, 4S), (2S, 3S, 4R)-epoxyprolines and aminohydroxyprolines

25, 3R, 4S- and 25, 38, 4R-epoxy-L-prolines were synthesised from trans- 4-hydroxy-L-proline. Assignment of the stereochemical configurations of the epoxy prolines was achieved by n.O.e. studies and chemical correlation. The synthetic utility of the protected epoxides was investigated briefly by ring opening with NAN3, followed by deprotection to give aminohydroxy prolines.

Substrate specificity of proline 4-hydroxylase: Chemical and enzymatic synthesis of 2S,3R,4S-epoxyproline

The substrate specificity of L-proline 4-hydroxylase, a 2-oxoglutarate dependent dioxygenase from Streptomyces griseoviridus P8648, was investigated. Preliminary assays measuring turnover of 2-oxyglutarate indicated 3,4-dehydro-L-proline was an efficient