Solid-Phase, Pd-Catalyzed Silicon-Aryl Carbon Bond Formation. Synthesis of Sansalvamide A Peptide

Abstract

A palladium-catalyzed silicon-aryl carbon bond formation on solid-phase is reported. A phenylalanine silane resin was prepared directly from protected iodo-substituted phenylalanine with butyl diethylsilane polystyrene in one step. A rapid and high-yield solid-phase synthesis of sansalvamide A peptide was achieved from the phenylalanine silane resin. [reaction: see text]

Rapid Virulence Annotation (RVA): Identification of virulence factors using a bacterial genome library and multiple invertebrate hosts

“…The identified sum formula of C 32 H 51 O 5 N 5 , from 1DF9 cosmid (RVA14), fits well with the structure of a cyclic pentapeptide. Interestingly, an identical sum formula is found in sansalvamide A peptides (22)(23)(24), synthetic derivatives of the depsipeptide natural product sansalvamide A that were isolated from a marine fungus and showed potent anti-cancer activity (25). Isolation of all identified compounds for detailed structure elucidation is currently underway.…”

Chemistry of Silicon‐Containing Amino Acids

“…The following are examples of acidic removal of Boc groups from trimethylsilylalanines 2 [16], silylphenylalanine 4 [48,49], and silylprolines 6 and 7 [43,50]. Hydrogenolysis of Cbz groups on silicon-substituted prolines 6 has been reported [37].…”

Bingchamides A and B, two novel cyclic pentapeptides from the Streptomyces bingchenggensis: fermentation, isolation, structure elucidation and biological properties

“…A number of analogs have been made. These sansalvamide A derivatives [6][7][8][9][10][14][15][16][17][18][19][20] have shown that they are privileged structures and exhibit potency against multiple targets in numerous cancer cell lines. The examples of potent cytotoxicity against pancreatic, colon, breast, prostate and melanoma cancers clearly indicate the potential of this compound class as a platform useful in targeting these cancers.…”

“…To evaluate their anticancer activities in vitro, we used the drug-resistant human cancer cell line HCT-116. [6][7][8][9][10] RESULTS AND DISCUSSION Structural elucidation Compound 1 was obtained as a colorless oil with the UV absorptions at l max of 232 and 275 nm. The molecular formula of 1 was established as C 40 H 51 N 5 O 5 on the basis of HRESI-MS and NMR analysis, which indicated the presence of 18 degrees of unsaturation.…”