32331-52-5Relevant academic research and scientific papers
Aldehyde-mediated bioconjugation: Via in situ generated ylides
Parmar, Sangeeta,Pawar, Sharad P.,Iyer, Ramkumar,Kalia, Dimpy
supporting information, p. 14926 - 14929 (2019/12/24)
A technically simple approach for rapid, high-yielding and site-selective bioconjugation has been developed for both in vitro and cellular applications. This method involves the generation of maleimido-phosphonium ylides via 4-nitrophenol catalysis under physiological conditions followed by their Wittig reactions with aldehyde-appended biomolecules.
Thiazolidin-5-imine Formation as a Catalyst-Free Bioorthogonal Reaction for Protein and Live Cell Labeling
Bi, Xiaobao,Yin, Juan,Rao, Chang,Balamkundu, Seetharamsing,Banerjee, Biplab,Zhang, Dingpeng,Zhang, Dawei,Dedon, Peter C.,Liu, Chuan-Fa
supporting information, p. 7790 - 7793 (2019/01/14)
A previously undescribed reaction involving the formation of a thiazolidin-5-imine linkage was developed for bioconjugation. Being highly specific and operating in aqueous media, this simple condensation reaction is used to chemoselectively label peptides, proteins, and living cells under physiological conditions without the need to use toxic catalysts or reducing reagents.
Catalytic asymmetric construction of chiral hydropyridazines via conjugate addition of N-monosubstituted hydrazones to enones
Wu, Wenbin,Yuan, Xiaoqian,Hu, Juan,Wu, Xinxin,Wei, Yuan,Liu, Zunwu,Lu, Junzhu,Ye, Jinxing
supporting information, p. 4524 - 4527 (2013/09/24)
The first example of a highly enantioselective and scalable formal diaza-ene reaction between N-monosubstituted hydrazones and enones catalyzed by a simple chiral primary-second diamine salt has been developed. The catalytic process provides a highly prac
Strain-promoted cycloadditions of cyclic nitrones with cyclooctynes for labeling human cancer cells
McKay, Craig S.,Blake, Jessie A.,Cheng, Jenny,Danielson, Dana C.,Pezacki, John Paul
supporting information; experimental part, p. 10040 - 10042 (2011/10/12)
Strain-promoted cycloadditions of cyclic nitrones with cyclooctynes proceed with rate constants up to 3.38 ± 0.31 M-1 s-1 in CD3CN, or 59 times faster than the analogous reaction of azides. This highly specific modular labeling strategy can be applied for direct labeling of proteins and for live cell imaging of cancer cells. The Royal Society of Chemistry 2011.
Access to α-functionalized glycine derivatives with arylboronic acid via imino amides
Zhao, Liang,Liao, Xiaohong,Li, Chao-Jun
scheme or table, p. 2953 - 2956 (2010/01/21)
An efficient approach was developed for the α-arylation of imino amides with arylboronic acids. Different substrates were examined for this arylation reaction. For the α-arylation of N-phenylimino amide, due to the electron-withdrawing properties of the phenyl group, the tautomerization between the amide and the iminol is more difficult. Thus, low reaction rate and low conversion were observed. This phenomenon supported our previously proposed mechanism for the arylation of -amino acid derivatives. Meanwhile, this method provides an alternative approach for the synthesis of α-functionalized glycine derivatives. Georg Thieme Verlag Stuttgart.
Amino amides, peptides and peptidomimetics
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Page 13-14, (2010/02/05)
Synthetic methods and compounds involving amino amides, peptides and peptidomimetics. Amino amide derivatives are prepared via the one-step three-component reaction of a glyoxamide, an amine, and an organoboron derivative. Conversion of the product to another glyoxamide intermediate allows the iterative use of this chemistry for the synthesis of peptides and peptidomimetics.
Synthesis of a peptidomimetic HCMV protease inhibitor library
Xu, Ping,Lin, Wenwei,Zou, Xiaomin
, p. 1017 - 1026 (2007/10/03)
The human cytomegalovirus (HCMV) protease catalyzes the maturational process of the herpes virus assembly protein and plays a key role during the manufacture of viral capsid, and so is an attractive target for potential anti-herpes-virus agents with novel structures and new mechanisms. In this work, a peptidomimetic skeleton was designed and a chemical library containing 32 compounds with different substitutions on the skeleton was prepared by the oxidation of a precursor library, which was constructed from four types of building blocks: 4 carboxylic acids, 2 amines, 2 aldehydes and 2 isocyanides, based on multicomponent condensation following liquid phase strategies. The syntheses of the key building block isocyanides are presented.
