Cyclosophorohexadecaose and succinoglycan monomers as catalytic carbohydrates for the Strecker reaction.
Some microbial carbohydrates have been used as catalysts for the multicomponent Strecker reaction using trimethylsilyl cyanide (TMSCN). Alpha-Cyclosophorohexadecaose (alpha-C16) derived from Xanthomonas species and succinoglycan monomers derived from Rhizobium species acted as catalytic carbohydrates in the mixture solutions of methanol and water. Malonaldehyde bis(phenylimine) as a substrate was completely converted (yield: 100%) into its product to 100% by both alpha-C16 and the succinoglycan monomer (M2), having acetyl, pyruvyl, and succinyl groups as substituents after 1h. The catalytic abilities of the carbohydrates were dependent on the inherent structures of the substrates used in this study, where substrate 1 having a symmetrical structure rather than the others was favorably reacted with the alpha-C16 and M2. Through this study, we suggest that the microbial carbohydrates used in this study could be expected to be environmentally-benign catalysts for the synthesis of alpha-aminonitriles.
Lee
Sanghoo
S
Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul 143-701, Republic of Korea.
Cho
Eunae
E
Kwon
Chanho
C
Jung
Seunho
S
D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D002621:Chemistry / Q000379:methods; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol / Q000737:chemistry; D008956:Models, Chemical; D009570:Nitriles / Q000737:chemistry; D011135:Polysaccharides, Bacterial / Q000737:chemistry*; D012231:Rhizobium / Q000378:metabolism; D014466:Ultraviolet Rays; D014867:Water / Q000737:chemistry; D014974:Xanthomonas / Q000378:metabolism; D047391:alpha-Cyclodextrins / Q000737:chemistry*
D002241:Carbohydrates; D009570:Nitriles; D011135:Polysaccharides, Bacterial; D047391:alpha-Cyclodextrins; C098291:alpha-cyclosophorohexadecaose; D014867:Water; C056779:succinoglycan; D000432:Methanol