103188-43-8Relevant articles and documents
Mining Plants for Bacterial Quorum Sensing Modulators
David, Shimrit,Mandabi, Aviad,Uzi, Shaked,Aharoni, Asaph,Meijler, Michael M.
, p. 247 - 252 (2018)
The bacterial plant pathogen Agrobacterium tumefaciens uses quorum sensing (QS) in order to regulate the transfer of DNA into the host plant genome, and this results in the induction of crown gall tumors. The deleterious results of these infections are wi
Synthesis of Amides with Remote Stereocenters by Catalytic Asymmetric γ-Alkynylation of α,β-Unsaturated Amides
Wang, Zi-Xuan,Bai, Xiao-Yan,Yao, Han-Chao,Li, Bi-Jie
, p. 14872 - 14875 (2016)
An iridium-catalyzed enantioselective hydroalkynylation of α,β-unsaturated amides was described. The selectivity of this reaction is distinct from that observed in many catalytic hydroalkynylations of α,β-unsaturated carbonyl compounds. It occurs selectively at the γ instead of the β position. Preliminary mechanistic studies suggest that the reaction proceeds through alkene isomerization followed by hydroalkynylation. This method provides a straightforward route for the synthesis of amides with a remote stereocenter at the γ position.
Allenone-Mediated Racemization/Epimerization-Free Peptide Bond Formation and Its Application in Peptide Synthesis
Wang, Penghui,Wang, Xuewei,Wang, Zhengning,Zhao, Junfeng
supporting information, p. 10374 - 10381 (2021/07/26)
Allenone has been identified as a highly effective peptide coupling reagent for the first time. The peptide bond was formed with an α-carbonyl vinyl ester as the key intermediate, the formation and subsequent aminolysis of which proceed spontaneously in a racemization-/epimerization-free manner. The allenone coupling reagent not only is effective for the synthesis of simple amides and dipeptides but is also amenable to peptide fragment condensation and solid-phase peptide synthesis (SPPS). The robustness of the allenone-mediated peptide bond formation was showcased incisively by the synthesis of carfilzomib, which involved a rare racemization-/epimerization-free N to C peptide elongation strategy. Furthermore, the successful synthesis of the model difficult peptide ACP (65-74) on a solid support suggested that this method was compatible with SPPS. This method combines the advantages of conventional active esters and coupling reagents, while overcoming the disadvantages of both strategies. Thus, this allenone-mediated peptide bond formation strategy represents a disruptive innovation in peptide synthesis.
Water-soluble alkyne amide condensing agent as well as preparation method and application thereof
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Paragraph 0261-0266, (2021/02/10)
The invention discloses a water-soluble alkyne amide condensing agent and an application method of the water-soluble alkyne amide condensing agent in synthesis of amide, polypeptide, ester and thioester compounds. The alkyne amide condensing agent has good performance and can efficiently and conveniently promote formation of amide bonds and ester bonds, alpha-chiral centers of carboxylic acid is free of racemization in the reaction process, carboxylic acid activation and a subsequent amidation reaction can be performed spontaneously, and extra additives and catalysts are not needed. After amidation and esterification reactions are finished, reaction by-products and the excessive alkyne amide condensing agent can be converted into substances capable of being dissolved in water through treatment by a weakly-acidic aqueous solution, and then high-purity products can be obtained through extraction and/or recrystallization. The whole process is simple to operate, has the characteristics ofconvenience in purification, wide application range, economic performance and environmental protection, conforms to the direction of green chemistry in modernization, and has good application prospects.
