13504-85-3

Usage

Chemical Properties

Viscous Oil

Uses

A competitive inhibitor of porcine kidney prolidase.

InChI:InChI=1/C13H15NO5/c15-10-6-11(12(16)17)14(7-10)13(18)19-8-9-4-2-1-3-5-9/h1-5,10-11,15H,6-8H2,(H,16,17)/t10-,11+/m1/s1

Upstream product

• 501-53-1 benzyl chloroformate 
• 2584-71-6 cis-hydroxy-D-proline 
• 7536-89-2 trimethylsilyl (2S,4R)-4-(trimethylsilyoxy)pyrrolidine-2-carboxylate 
• 51-35-4 4-hydroxyproline 
• 117811-78-6 methyl (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate 
• 64187-47-9 1-benzyloxycarbonyl-4-keto-L-proline 
• 85201-91-8 (2S,4R)-4-tert-butoxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 
• 51-35-4 4R-4-hydroxyproline 

Downstream Products

• 13504-86-4 (2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline 
• 159551-87-8 (2S,4R)-N^α-Cbz-4-[(p-toluenesulfonyl)oxy]proline benzyl ester 
• 329191-63-1 (2S,4S)-N^α-Cbz-4-bromoproline benzyl ester 
• 329191-66-4 (2S,4R)-N^α-Cbz-4-aminoproline benzyl ester 
• 329191-64-2 (2S,4R)-N^α-Cbz-4-azidoproline benzyl ester 
• 329191-55-1 (2S,4S)-N^α-Cbz-4-azidoproline benzyl ester 
• 329191-68-6 (2S,4R)-N^α-Cbz-4-N,N'-di-Boc-guanidinoproline benzyl ester 
• 117811-79-7 (2S,4R)-1-benzyloxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxypyrrolidine 
• 127768-11-0 (2S,4R)-1-benzyloxycarbonyl-2-(2-oxoethyl)oxymethyl-4-methanesulfonyloxypyrrolidine 
• 117811-82-2 (2S,4R)-2-[(2-aminoethyl)oxymethyl]-1-benzyloxycarbonyl-4-methanesulfonyloxypyrrolidine 
• 127768-04-1 (2S,4R)-1-benzyloxycarbonyl-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxypyrrolidine 
• 127768-05-2 (2S,4R)-1-benzyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-methanesulfonyloxypyrrolidine 
• 199998-83-9 (2S,4R)-1-benzyloxycarbonyl-2-(2-hydroxypropyl)oxymethyl-4-methanesulfonyloxypyrrolidine 
• 199998-84-0 (2S,4R)-1-benzyloxycarbonyl-2-(2-fluoropropyl)oxymethyl4-methanesulfonyloxypyrrolidine 

Relevant academic research and scientific papers

A recyclable and highly stereoselective multi-fluorous proline catalyst for asymmetric aldol reactions

A recyclable fluorous proline catalyst with high stereoselectivity that functions as a catalyst for asymmetric aldol reactions is described. Its high stereoselectivity and facile recovery are achieved by employing a multi-fluorous tag attachment strategy. Although a gradual decrease was observed with respect to the catalytic activity, the catalyst can be separated from the reaction mixture by adsorption onto FluoroFlash and can be reused in that form for a maximum of five times while maintaining a high stereoselectivity.2019 Elsevier Ltd. All rights reserved.

An Immucillin-Based Transition-State-Analogous Inhibitor of tRNA-Guanine Transglycosylase (TGT)

Shigellosis is one of the most severe diarrheal diseases worldwide without any efficient treatment so far. The enzyme tRNA-guanine transglycosylase (TGT) has been identified as a promising target for small-molecule drug design. Herein, we report a transition-state analogue, a small, immucillin-derived inhibitor, as a new lead structure with a novel mode of action. The complex inhibitor synthesis was accomplished in 18 steps with an overall yield of 3 %. A co-crystal structure of the inhibitor bound to Z. mobilis TGT confirmed the predicted conformation of the immucillin derivative in the enzyme active site.

An improved synthesis of (lS,4S)-2-oxa-5-azabicyclo[2.2.1]heptane

An improved and efficient method for synthesis of (lS,4S)-2-oxa-5- azabicyclo[2.2.1]heptane (1) from trans-4-hydroxy-l-proline was developed. Using benzyloxycarbonyl (Cbz) as protection group of amine, the reactions were in mild conditions, and the title compound 1 was accomplished in six steps in overall yield of 70%.

Unveiling epidithiodiketopiperazine as a non-histone arginine methyltransferase inhibitor by chemical protein methylome analyses

We present a chemical methylome analysis platform to evaluate the inhibitory activity of small molecules towards poorly characterized protein methyltransferases (PMTs), facsilitating to identify syn-HyPA-ETP-2 as a non-histone arginine methyltransferase inhibitor.

Design and synthesis of fluorinated peptides for analysis of fluorous effects on the interconversion of polyproline helices

The unique interaction between fluorine atoms has been exploited to alter protein structures and to develop synthetic and analytical applications. To expand such fluorous interaction for novel applications, polyproline peptides represent an excellent molecular nanoscaffold for controlling the presentation of perfluoroalkyl groups on their unique secondary structure. We develop approaches to synthesis fluorinated peptides to systematically investigate how the number, location and types of the fluorous groups on polyproline affect the conformation by monitoring the transition between the two major polyproline structures PPI and PPII. This work provides valuable information on how fluorous interaction affects the peptide structure and also benefits the design of functional fluorous molecules.

Preparation method of intermediate

The invention relates to a preparation method of an intermediate, and belongs to the field of medicinal chemistry. The preparation method comprises at least one reaction step of an addition elimination reaction, a cyclization reaction, a reduction reaction, a decarboxylation reaction and a hydrogenation reaction. According to the method disclosed by the invention, the target intermediate with a single configuration can be simply and conveniently obtained, chiral resolution is effectively avoided, the yield is improved, the cost is reduced, and industrial production is facilitated.

Practical Gram-Scale Synthesis of Iboxamycin, a Potent Antibiotic Candidate

A gram-scale synthesis of iboxamycin, an antibiotic candidate bearing a fused bicyclic amino acid residue, is presented. A pivotal transformation in the route involves an intramolecular hydrosilylation-oxidation sequence to set the ring-fusion stereocenters of the bicyclic scaffold. Other notable features of the synthesis include a high-yielding, highly diastereoselective alkylation of a pseudoephenamine amide, a convergent sp3-sp2 Negishi coupling, and a one-pot transacetalization-reduction reaction to form the target compound's oxepane ring. Implementation of this synthetic strategy has provided ample quantities of iboxamycin to allow for its in vivo profiling in murine models of infection.

LINCOSAMIDE ANTIBIOTICS AND USES THEREOF

Provided are compounds of Formula (I) for the treatment of infectious and inflammatory diseases. The compounds described herein are lincosamides modified at the amino acid (southern) region. The compounds may have further modification at the C-7 position of the aminooctose (northern) region, thus distinguishing them from lincomycin and clindamycin. Also provided are methods for preparing the compounds, pharmaceutical compositions comprising the compounds, and methods of treating infectious diseases using the disclosed compounds.

FUSED HETEROCYCLIC BENZODIAZEPINE DERIVATIVES AND USES THEREOF

The present disclosure provides compounds and compositions capable of extending lifespan, and methods of use thereof.

NOVEL BENZODIAZEPINE DERIVATIVES AND USES THEREOF

The present disclosure provides compounds and compositions capable of extending lifespan, and methods of use thereof.