Phaseolin

Other common phytoalexins in food materials are pisatin, cinnamylphenols, glyceolin, phaseolin [13401 -40-6] (14), and 5-deoxykieritol in peas, beans, soybeans, and lima beans viniferin in grapes momilactones and ory2alexins in rice a-tomatine in tomato lubimen in eggplant and capsidiol in green peppers. 

Storage proteins Ovalbumin Casein Zein Phaseolin Eerritin... 

SANTORO L G, GRANT G, puszTAi A (1997) Effects of short-term feeding of rats with a highly purified phaseolin preparation. Plant foods for Human Nutr. 51 61-70. 

A relationship was observed between phaseolin pattern and seed type. Cultivars with T, C, H, and A phaseolin types on the average have larger seeds than cultivars... 

Fig. 7.3 Polymerase chain reaction amplification of part of the phaseolin genes surrounding the 15 repeat. 1 T phaseolin (Andean) 2 S phaseolin (Mesoamerican) 3 1 phaseolin (Ecuador and northern Peru) (Kami et al. 1995)...

Kami J, Becerra-Velasquez V, Debouck DG, Gepts P (1995) Identification of presumed ancestral DNA sequences of phaseolin in Phaseolus vulgaris. Proc Natl Acad Sci USA 92 1101-1104 Kaplan L (1981) What is the origin of common bean Econ Bot 35 240-254 Kaplan L, Lynch TF (1999) Phaseolus (Fabaceae) in archaeology AMS radiocarbon dates and their significance for pre-colombian agriculture. Econ Bot 53 261-272... 

Lioi L (1989) Geographical variation of phaseolin patterns in an old world collection of Phaseolus vulgaris. Seed Sci Technol 17 317-324... 

Renaud and co-workers used 78 for the synthesis of (-)-phaseolinic acid (6) and (-)-pertusarinic acid (8) (Scheme 12) [32, 33]. Radical addition of dimethyl phenylselenomalonate to 78 proceeded with rearrangement of the bicyclics to yield the seleno-acetal 79 [34]. After reductive deselenylation and Baeyer-Villiger oxidation treatment of 80 with BU4NI and BBr3 led to a simultaneous cleavage of the ether, the lactone, and the methyl ester func-... 

The required side-chain for (-)-pertusarinic acid (8) was introduced by a mixed Kolbe electrolysis with 85 [36], elegantly demonstrating the value of this process for natural product synthesis in the presence of various functional groups. In an analogous way (-)-phaseolinic acid (6) was synthesized by reacting pentanoic acid in a mixed Kolbe electrolysis with 84 to 88. 

Strategy should also be applicable to paraconic acids, and indeed, the synthesis of (+)-phaseolinic acid (6) as well as (-)-methylenolactocin (11) has successfully been achieved this way (Scheme 24) [61]. This approach is especially advantageous if the precursors are readily available on large scale to compensate for the principle loss of at least 50% caused by the presence of the undesired enantiomer. Thus, a mixture of the lactones ( )-151 and ( )-152 is available in a single step from the ketodiester 150 [5c, 62] via a reduc-tion-lactonization sequence. After separation, ( )-151 was transformed into racemic ( )-153, which was hydrolyzed by pig liver esterase (PLE) to yield (+)-phaseolinic acid ((+)-6) in up to 94% ee. Alternatively, the remaining (-)-153 could be obtained in up to 96% ee, which could be hydrolyzed to (-)-phaseolinic acid ((-)-6). 

Legumin, from Pea. (Osborne and Clapp.) Amandin, from Almond. (Osborne and Clapp Osborne and Gilbert.) Glycinin, from SoyBean. (Osborne and Clapp.) Phaseolin, from White Kidney Bean. (Cisborne and Clapp.) Protein of Maize. (Osborne and Clapp.)... 

The utility and efficiency of this methodology is demonstrated by the first catalytic asymmetric synthesis of (—)-phaseolinic acid , a natural product displaying useful antifungal, antitumor and antibacterial properties, as illustrated in equation 110. 

Lawrence, M.C., Izard, T., Beuchat, M., Blagrove, R.J., Colman, P.M. (1994). Structure of phaseolin at 2.2 A resolution. Implication for a common vicilin/legumin structure and the genetic engineering of seed storage proteins. Journal of Molecular Biology, 238, 748-776. 

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