Stereocontrolled Synthesis of Onchidins

Peng, Yungui; Pang, Heung Wing; Ye, Tao

doi:10.1021/ol048437p

Cited by 27 publications

(6 citation statements)

References 15 publications

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“…The 2‐methyl‐3‐amino butyric acid ( 14 ) was prepared from N ‐Cbz‐ D ‐alanine by a three‐step sequence involving the formation of a diazoketone21 followed by a Wolff rearrangement21, 22 and a diastereoselective methylation 10t. 23…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis and Biological Evaluation of Grassypeptolide A

Liu

Wang

et al. 2013

Chemistry A European J

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Herein, we describe in full our investigations into the synthesis of grassypeptolide A (1) in 17 linear steps with an overall yield of 11.3 %. In particular, this work features the late-stage introduction of sensitive bis(thiazoline) heterocycles and 31-membered macrocyclization conducted at the sterically congested secondary amide site in superb conversion (72 % yield). Biological evaluation indicated that grassypeptolide A significantly inhibited cancer cell proliferation in a dose-dependent manner. It induced cancer cell apoptosis, which was associated with increased cleavage of poly(ADP-ribose) polymerase (PARP) and decreased expression of bcl-2 and bcl-xL. Furthermore, grassypeptolide A also caused cell cycle redistribution by increasing cells in the G1 phase and decreasing cells in the S and G2 phases. In addition, cell cycle arrest was correlated with downregulation of cyclin D and upregulation of p27 and p21.

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Section: Resultsmentioning

confidence: 99%

Total Synthesis and Biological Evaluation of Grassypeptolide A

Liu

Wang

et al. 2013

Chemistry A European J

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“…603 The structure proposed for onchidin, 604 a cytotoxic depsipeptide from a pulmonate Onchidium species but possibly of cyanobacterial origin, has been synthesised and exhibited different spectroscopic data to that observed for the natural product. 605 A full account of the stereoselective synthesis of (+)-brasilenyne, an antifeedant haloether from a sea hare Aplysia brasiliana, 264 has been reported. 266 Enantioselective syntheses of (-)-tochuinyl acetate 668 and (-)-dihydrotochuinyl acetate 669 606 defined the absolute configurations of the sesquiterpenes that were isolated from a nudibranch Tochuina tetraquetra and its dietary soft coral Gersemia rubiformis.…”

Section: Molluscsmentioning

confidence: 99%

Marine natural products

et al. 2006

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This review covers the literature published in 2004 for marine natural products, with 693 citations (491 for the period January to December 2004) referring to compounds isolated from marine microorganisms and phytoplankton, green algae, brown algae, red algae, sponges, coelenterates, bryozoans, molluscs, tunicates and echinoderms. The emphasis is on new compounds (716 for 2004), together with their relevant biological activities, source organisms and country of origin. Biosynthetic studies (8), and syntheses (80), including those that lead to the revision of structures or stereochemistries, have been included.

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“…Mass spectra were recorded using a Finnigan MAT 95 sector field spectrometer (HRMS, CI) or a Daltonics maXis 4G hr-ToF spectrometer (HRMS, ESI) from Bruker (Billerica, MA, USA). The Alloc-protected amino acids (Alloc-AlaOH [ 79 ], Alloc- N -Me-LeuOH [ 80 , 81 ] and Alloc- N’ -Me-TrpOH [ 39 ]) were synthesized according to protocols known from the literature.…”

Section: Methodsmentioning

confidence: 99%

Total Synthesis and Biological Evaluation of Modified Ilamycin Derivatives

2022

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Ilamycins/rufomycins are marine cycloheptapeptides containing unusual amino acids. Produced by Streptomyces sp., these compounds show potent activity against a range of mycobacteria, including multidrug-resistant strains of Mycobacterium tuberculosis. The cyclic peptides target the AAA+ protein ClpC1 that, together with the peptidases ClpP1/ClpP2, forms an essential ATP-driven protease. Derivatives of the ilamycins with a simplified tryptophane unit are synthesized in a straightforward manner. The ilamycin derivative 26 with a cyclic hemiaminal structure is active in the nM-range against several mycobacterial strains and shows no significant cytotoxicity. In contrast, derivative 27, with a glutamic acid at this position, is significantly less active, with MICs in the mid µM-range. Detailed investigations of the mode of action of 26 indicate that 26 deregulates ClpC1 activity and strongly enhances ClpC1-WT ATPase activity. The consequences of 26 on ClpC1 proteolytic activities were substrate-specific, suggesting dual effects of 26 on ClpC1-WT function. The positive effect relates to ClpC1-WT ATPase activation, and the negative to competition with substrates for binding to the ClpC1 NTD.

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Stereocontrolled Synthesis of Onchidins

Abstract: [structure: see text] The first total synthesis of a molecule possessing the stereochemistry proposed for onchidin is described. The structure synthesized appears to be different from that of the marine natural product.

Cited by 27 publications

References 15 publications

Total Synthesis and Biological Evaluation of Grassypeptolide A

Total Synthesis and Biological Evaluation of Grassypeptolide A

Marine natural products

Total Synthesis and Biological Evaluation of Modified Ilamycin Derivatives

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