20824-29-7Relevant articles and documents
Total Synthesis of (-)-Strictosidine and Interception of Aryne Natural Product Derivatives "strictosidyne" and "strictosamidyne"
Anthony, Sarah M.,Tona, Veronica,Zou, Yike,Morrill, Lucas A.,Billingsley, John M.,Lim, Megan,Tang, Yi,Houk,Garg, Neil K.
, p. 7471 - 7479 (2021/05/26)
Monoterpene indole alkaloids are a large class of natural products derived from a single biosynthetic precursor, strictosidine. We describe a synthetic approach to strictosidine that relies on a key facially selective Diels-Alder reaction between a glucosyl-modified alkene and an enal to set the C15-C20-C21 stereotriad. DFT calculations were used to examine the origin of stereoselectivity in this key step, wherein two of 16 possible isomers are predominantly formed. These calculations suggest the presence of a glucosyl unit, also inherent in the strictosidine structure, guides diastereoselectivity, with the reactive conformation of the vinyl glycoside dienophile being controlled by an exo-anomeric effect. (-)-Strictosidine was subsequently accessed using late-stage synthetic manipulations and an enzymatic Pictet-Spengler reaction. Several new natural product analogs were also accessed, including precursors to two unusual aryne natural product derivatives termed "strictosidyne"and "strictosamidyne". These studies provide a strategy for accessing glycosylic natural products and a new platform to access monoterpene indole alkaloids and their derivatives.
A (S)- tetrahydro Angustine derivative and its preparation and use (by machine translation)
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Paragraph 0037; 0038, (2018/05/16)
The present invention provides a (S)- tetrahydro Angustine derivatives and their pharmaceutically acceptable salts, the use of nucleotide synthetase catalytic tryptamine and crack link vomica alkali synthetic nucleotide as the initiator, obtained through a series of structural modification. The invention synthesizes the traditional medicinal chemistry to a sole chiral synthesis of a plurality of works and nuclear compound, such compound has outstanding in vitro topoisomerase I inhibitory activity HepG2 with the in vitro anti-tumor activity, can be in the preparation topoisomerase I inhibitor anti-tumor drug in the application. With the following formula (I) structure of the general formula: . (by machine translation)
Engineering strictosidine synthase: Rational design of a small, focused circular permutation library of the β-propeller fold enzyme
Fischereder, Eva,Pressnitz, Desiree,Kroutil, Wolfgang,Lutz, Stefan
, p. 5633 - 5637 (2015/01/09)
Strictosidine synthases catalyze the formation of strictosidine, a key intermediate in the biosynthesis of a large variety of monoterpenoid indole alkaloids. Efforts to utilize these biocatalysts for the preparation of strictosidine analogs have however been of limited success due to the high substrate specificity of these enzymes. We have explored the impact of a protein engineering approach called circular permutation on the activity of strictosidine synthase from the Indian medicinal plant Rauvolfia serpentina. To expedite the discovery process, our study departs from the usual process of creating a random protein library, followed by extensive screening. Instead, a small, focused library of circular permutated variants of the six bladed β-propeller protein was prepared, specifically probing two regions which cover the enzyme active site. The observed activity changes suggest important roles of both regions in protein folding, stability and catalysis.
