Chiral resolution function with immobilized food proteins.
We confirmed that an NAD(P)+-dependent secondary alcohol dehydrogenase (NAD(P)-E) can be easily and effectively isolated from pea, soybean, and wheat proteins immobilized with calcium alginate gel (IPP, ISP, and IWP, respectively). The estimated molecular mass of NAD(P)-E is 138.7 kDa, and the concentrations of NAD(P)-E in solution are 36.2 (IPP), 53.9 (ISP), and 93.7 (IWP) microg/mL. The NAD(P)-E oxidizes only (R)-isomers highly enantioselectively; thus, greater than 99% ee(s) of (S)-isomers can be obtained from corresponding rac-aryl methyl carbinols (1, 2a-6a, and 2b-7b). The amount of food protein needed for 1 g of substrate (B/S ratio) is approximately 20. Thus, in comparison to current biocatalysts, certain food proteins can serve as asymmetric reagent bases, providing easily obtained, low-cost natural catalysts with stereoselectivity, regioselectivity, and substrate specificity that work under mild conditions for asymmetric synthesis of organic compounds. Moreover, this "fourth" function of food may help build a sustainable society by synthesizing optically active secondary alcohols in an environmentally friendly manner.
Nagaoka
Hiroyuki
H
Sanyo Shokuhin Co., Ltd. R & D, 555-4 Asakura, Maebashi, Gunma 371-0811, Japan. nagaoka1@sea.plala.or.jp
D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D000464:Alginates / Q000737:chemistry; D004789:Enzyme Activation; D004795:Enzyme Stability; D004800:Enzymes, Immobilized / Q000737:chemistry*; D005524:Food Technology / Q000379:methods*; D020723:Glucuronic Acid / Q000737:chemistry; D006603:Hexuronic Acids / Q000737:chemistry; D008970:Molecular Weight; D009252:NADPH Dehydrogenase / Q000737:chemistry* / Q000378:metabolism; D018532:Pisum sativum / Q000201:enzymology*; D010940:Plant Proteins / Q000737:chemistry*; D030262:Soybean Proteins / Q000737:chemistry; D013025:Glycine max / Q000201:enzymology*; D013237:Stereoisomerism; D013379:Substrate Specificity; D014908:Triticum / Q000201:enzymology*
D000438:Alcohols; D000464:Alginates; D004800:Enzymes, Immobilized; D006603:Hexuronic Acids; D010940:Plant Proteins; D030262:Soybean Proteins; D020723:Glucuronic Acid; D009252:NADPH Dehydrogenase