95656-84-1

Upstream product

• 117997-81-6 5-(benzyloxy)-2-(tert-butoxycarbonylamino)-5-oxopentanoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 57294-38-9 N-(tert-butoxycarbonyl)-4-aminobutanoic acid 
• 100-39-0 benzyl bromide 
• 13574-13-5 Boc-Glu(OBzl)-OH 
• 100-51-6 benzyl alcohol 

Downstream Products

• 936836-78-1 benzyl 4-[[{3-[(tert-butoxycarbonyl)amino]propylamino}thiocarbonyl]amino]butanoate 
• 78287-52-2 4-aminobutanoic acid benzyl ester hydrochloride 

Relevant academic research and scientific papers

ANTIBACTERIAL ANTISENSE AGENTS

The invention relates to improved ANTISENSE agents for the treatment of gram-negative bacterial infections. Compounds of the invention utilise an Antibiotic-Assisted Translocation; AAT' platform to improve influx into bacterial cells through enhanced permeability, providing improved intracellular exposure of the ANTISENSE AGENT and superior treatment of the infection.

Synthesis and biological evaluations of cytotoxic and antiangiogenic triterpenoids-jacaranone conjugates

Background: The development of antiangiogenic agents arises as a more effective and selective therapeutic approach for the treatment of cancer. In addition to reduced acute toxicity, the efficacy of chemotherapy could be improved when administered in combination specific antiangiogenic with cytotoxic agents. The conjugation or hybridization of bifunctional molecules is one of the alternative rational design strategies for co-administration of anticancer drugs. Objective and Methods: The goal of this work is to prepare the conjugates of an antiangiogenic triterpene, 3-oxo oleanolic acid, and structurally related triterpenoids with a cytotoxic semibenzoquinone, jacaranone. The cytotoxic, antiproliferative and antiangiogenic activities of segments and conjugates were determined. The possible targets of conjugates 6a-6h were predicted using Similarity Ensemble Approach (SEA). Results: The results showed that these conjugates are more potent in both cytotoxic and antiangiogenic assays than their corresponding parent molecules, and are also selectively more active against melanoma cells B16 and metastatic B16BL6 than the two other cancer cell lines (A549 and MCF-7) tested. The predicted antiangiogenesis related targets could involve glycogen phosphorylase, neuraminidase, interferon gamma, and tubulin beta chain. Conclusion: The bifunctional conjugates could be useful as dual acting antitumor/antigiogenic agents.

Photocatalytic decarboxylative reduction of carboxylic acids and its application in asymmetric synthesis

The decarboxylative reduction of naturally abundant carboxylic acids such as α-amino acids and α-hydroxy acids has been achieved via visible-light photoredox catalysis. By using an organocatalytic photoredox system, this method offers a mild and rapid entry to a variety of high-value compounds including medicinally relevant scaffolds. Regioselective decarboxylation is achieved when differently substituted dicarboxylic acids are employed. The application of this method to the synthesis of enantioenriched 1-aryl-2,2,2-trifluoroethyl chiral amines starting from natural α-amino acids further testifies to the utility of the developed photocatalytic decarboxylative reduction protocol.

Enzymatic removal of carboxyl protecting groups. 2. Cleavage of the benzyl and methyl moieties

Enzymes are versatile reagents for the efficient removal of methyl and benzyl protecting groups. An esterase from Bacillus subtilis (BS2) and a lipase from Candida antarctica (CAL-A) allow a mild and selective removal of these moieties in high yields without affecting other functional groups.

The Lindlar Catalyst Revitalized: A Highly Chemoselective Method for the Direct Conversion of Azides to N-(tert-Butoxycarbonyl)amines

An exceptionally chemoselective method for the direct conversion of azides to N-(tert-butoxycarbonyl)-protected amines under catalytic transfer-hydrogenation conditions, using the Lindlar catalyst, is reported. The extremely labile functional groups such as N-Cbz, benzyl ester are shown to be inert under the reaction conditions. The present method allows us to synthesize orthogonally protected (N-Cbz and N-Boc) 1,2-diamino systems, which will be immensely useful in organic synthesis.

MANIPULATION OF THE CARBOXYL GROUPS OF α-AMINO-ACIDS AND PEPTIDES USING RADICAL CHEMISTRY BASED ON ESTERS OF N-HYDROXY-2-THIOPYRIDONE

Photolysis of α-amino-acid or peptide esters derived from N-hydroxy-2-thiopyridone in the presence of t-butylthiol affords the expected decarboxylation products in good yield.The reaction can be applied to the α-carboxyl or to the side chain carboxyl of g

Reductive Radical Decarboxylation of Amino-acids and Peptides

Radicals generated from N-protected α-amino-acids by photolysis of their N-hydroxypyridine-2-thione esters at room temperature are efficiently quenched by t-butyl thiol to give decarboxy-acids; comparable reactions have been carried out on the side chain carboxy groups of suitable protected aspartic and glutamic acids.