38678-58-9

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
PHENOXYACETIC ACID N-HYDROXYSUCCINIMIDE ESTER is used as an intermediate for the synthesis of various pharmaceuticals and agrochemicals, facilitating the creation of new compounds with potential therapeutic and agricultural applications.
Used in Bioconjugation:
PHENOXYACETIC ACID N-HYDROXYSUCCINIMIDE ESTER is used as a bioconjugation agent for the attachment of proteins and peptides through amide bond formation, enabling the development of novel bioconjugates for research and medical applications.
Used in Peptide Synthesis:
In the field of peptide synthesis, PHENOXYACETIC ACID N-HYDROXYSUCCINIMIDE ESTER is used as a coupling agent to facilitate the formation of peptide bonds, allowing for the efficient synthesis of peptides with specific biological activities.
Used in Biomolecule Modification:
PHENOXYACETIC ACID N-HYDROXYSUCCINIMIDE ESTER is used as a modifying agent for the functionalization of biomolecules, such as proteins, nucleic acids, and carbohydrates, to enhance their properties or introduce new functionalities for various research and medical applications.

InChI:InChI=1/C12H11NO5/c14-10-6-7-11(15)13(10)18-12(16)8-17-9-4-2-1-3-5-9/h1-5H,6-8H2

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 122-59-8 2-phenoxyacetic acid 
• 701-99-5 Phenoxyacetyl chloride 

Downstream Products

• 92261-81-9 PhO-CH2CO-D-Ala(βCl)-D-Ala-OBzl 
• 92261-80-8 PhO-CH2CO-Ala(βCl)-Ala-OBzl 
• 96523-77-2 PhO-CH₂CO-D-Tyr-D-Ala-OBzl 
• 91661-95-9 20-dihydro-20-deoxy-20-(phenoxyacetamido)desmycosin 
• 96523-74-9 PhO-CH₂CO-Tyr-Ala-OBzl 
• 92261-86-4 PhO-CH₂CO-D-Arg(NO₂)-D-Ala-OBzl 
• 92261-85-3 PhOCH₂CO-Arg(NO₂)-Ala-OBzl 

Relevant academic research and scientific papers

Synthesis, biological evaluation, and structure-activity relationships of potent noncovalent and nonpeptidic cruzain inhibitors as anti-Trypanosoma cruzi agents

The development of cruzain inhibitors has been driven by the urgent need to develop novel and more effective drugs for the treatment of Chagas' disease. Herein, we report the lead optimization of a class of noncovalent cruzain inhibitors, starting from an inhibitor previously cocrystallized with the enzyme (Ki = 0.8 μM). With the goal of achieving a better understanding of the structure-activity relationships, we have synthesized and evaluated a series of over 40 analogues, leading to the development of a very promising competitive inhibitor (8r, IC50 = 200 nM, Ki = 82 nM). Investigation of the in vitro trypanocidal activity and preliminary cytotoxicity revealed the potential of the most potent cruzain inhibitors in guiding further medicinal chemistry efforts to develop drug candidates for Chagas' disease.

REACTIVITY OF N-HYDROXYSUCCINIMIDE ESTERS

The reactions of N-hydroxysuccinimide esters (OSu-esters) of benzyloxycarbonylamino acids and of simple carboxylic acid with p-anisidine in DMSO were studied kinetically at various temperatures.Activation parameters ΔH++ and ΔS++ for these data were determined.The rate constants for aminolysis of carboxylic acid esters fit the two-parameter Taft equation with reaction constants equal: ρ* = 1.08 and ρs = 1.1.The activation entropies are in the range -121.8 - -180.0 J/deg M.Transition state in these reactions is tetrahedral and zwitter ionic, in agreementwith the mechanism given by Cline and Hanna for aminolysis of succinimidyl benzoates.