183610-32-4Relevant academic research and scientific papers
Onchidin B: A new cyclodepsipeptide from the mollusc Onchidium sp.
Fernández, Rogelio,Rodríguez, Jaime,Qui?oá, Emilio,Riguera, Ricardo,Mu?oz, Luis,Fernández-Suárez, Miryam,Debitus, Cécile
, p. 11635 - 11643 (1996)
Onchidin B (4) is a cyclic depsipeptide isolated from the pulmonate mollusc Onchidium sp. Its structure was determined by extensive 2D-NMR, FABMS, tandem FAB MS/MS, selective hydrolysis, and synthesis. It contains four α-amino acids [two units of N-methyl
Precursor directed biosynthesis of an orthogonally functional erythromycin analogue: Selectivity in the ribosome macrolide binding pocket
Harvey, Colin J. B.,Puglisi, Joseph D.,Pande, Vijay S.,Cane, David E.,Khosla, Chaitan
supporting information; experimental part, p. 12259 - 12265 (2012/09/22)
The macrolide antibiotic erythromycin A and its semisynthetic analogues have been among the most useful antibacterial agents for the treatment of infectious diseases. Using a recently developed chemical genetic strategy for precursor-directed biosynthesis and colony bioassay of 6-deoxyerythromycin D analogues, we identified a new class of alkynyl- and alkenyl-substituted macrolides with activities comparable to that of the natural product. Further analysis revealed a marked and unexpected dependence of antibiotic activity on the size and degree of unsaturation of the precursor. Based on these leads, we also report the precursor-directed biosynthesis of 15-propargyl erythromycin A, a novel antibiotic that not only is as potent as erythromycin A with respect to its ability to inhibit bacterial growth and cell-free ribosomal protein biosynthesis but also harbors an orthogonal functional group that is capable of facile chemical modification.
Total synthesis of the proposed structure of cyclic hexadepsipeptide veraguamide A
Wang, Dongyu,Jia, Xian,Zhang, Ao
supporting information; experimental part, p. 7027 - 7030 (2012/09/22)
We have developed a practical method to assemble the proposed structure of natural product veraguamide A (1) by first preparing the three key fragments followed by optimization of the macrocyclization site. Although the synthetic product gave similar optical rotation to that reported for natural product, significant differences in the 1H and 13C NMR spectra were observed, especially the proton and carbon signals in the two N-MeVal moieties.
Synthesis of palau'amide and its diastereomers: confirmation of its stereostructure
Sugiyama, Hirokazu,Watanabe, Atsushi,Teruya, Toshiaki,Suenaga, Kiyotake
scheme or table, p. 7343 - 7345 (2010/03/01)
Four diastereomers of palau'amide (1-4), a cytotoxic cyclodepsipeptide, were synthesized. The 1H NMR spectrum of 1 was identical to that of natural palau'amide. This established the complete stereostructure of palau'amide.
