14254-45-6Relevant articles and documents
Synthesis and evaluation of a photoactive probe with a multivalent carbohydrate for capturing carbohydrate-lectin interactions
Chang, Tsung-Che,Lai, Chian-Hui,Chien, Chih-Wei,Liang, Chien-Fu,Adak, Avijit Kumar,Chuang, Yung-Jen,Chen, Yu-Ju,Lin, Chun-Cheng
, p. 1895 - 1906 (2014/01/06)
Lectins are ubiquitous carbohydrate-binding proteins of nonimmune origin that are characterized by their specific recognition of defined monosaccharide or oligosaccharide structures. However, the use of carbohydrates to study lectin has been restricted by the weak binding affinity and noncovalent character of the interaction between carbohydrates and lectin. In this report, we designed and synthesized a multifunctional photoaffinity reagent composed of a trialkyne chain, a masked latent amine group, and a photoreactive 3-trifluoromethyl-3- phenyl-diazirine group in high overall yield. Two well-defined chemistries, Huisgen-Sharpless click chemistry and amide bond coupling, were the key steps for installing the multivalent character and tag in our designed photoaffinity probe. The photolabeling results demonstrated that the designed probe selectively labeled the target lectin, RCA120 (Ricinus communis Agglutinin), in an E. coli lysate and an asialoglycoprotein receptor (ASGP-R) on intact HepG2 cell membranes. Moreover, the probe also enabled the detection of weak protein-protein interactions between RCA120 and ovalbumin (OVA).
SYNTHESIS OF AZA-CROWN COMPOUNDS BY INTRAMOLECULAR CYCLIZATION OF ω-AMINO ACIDS
Mikhura, I. V.,Formanovskii, A. A.
, p. 205 - 212 (2007/10/02)
A method for the synthesis of aza-crown compounds by the intramolecular cyclization of ω-amino acids with subsequent reduction of the lactam to a macrocyclic amine was developed. 1,8-Diazacyclotetradecane and 1,8-dioxa-4,11-diazacyclotetradecane was synthesized in preparative yields.The structural assignments were made using the IR, 1H and 13C NMR, and mass spectra.