Solid-Phase Synthesis and Cyclative Cleavage of Quorum Sensing ­Depsipeptide Analogues by Acylphenyldiazene Activation

Shigenaga, Akira; Moss, Jason A.; Ashley, Fawn T.; Kaufmann, Gunnar F.; Janda, Kim D.

doi:10.1055/s-2006-932468

Cited by 2 publications

(1 citation statement)

References 25 publications

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“…2001 年, Waldmann 等 [29] 利用该法也成功制备了骨架环六肽, stylostatin, 如图 3 所示. 此外, Janda 等 [30] 并将该方法用于多种骨架环肽分子的构建. 值得一提, 2004 年, Camareo 等 [31] 利用芳基肼氧化活化反应发展了 Fmoc 硫酯的合成方法.…”

Section: 端芳基酰基肼固定树脂unclassified

Recent Advances in Chemical Synthesis of Backbone Cyclized Peptides

Si¹,

Guo²,

Li³

et al. 2014

Chin. J. Org. Chem.

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Backbone cyclized peptides belong to a family of circular polypeptide molecules in which the carboxyl and amino termini are covalently linked by an amide bond. Over the last almost 20 years, the backbone cyclized peptides have been discovered in bacteria, fungi, plants and animals. Compared with their linear precursors, the backbone cyclized peptides have a head-to-tail cyclic backbone enabling them to resist enzymatic degradation and to improve their thermal and chemical stability. Remarkably, some of them even have cell membrane permeability. Due to their exceptionally intracellular stability and potent bioactivities, backbone cyclized peptide is emerging as one of the most interesting molecules in the area of drug discovery. To study the structure and function of backbone cyclized peptides in detail, it is necessary to develop efficient approaches for the synthesis of these molecules. Herein, the recent advances in chemical synthesis of backbone cyclized peptides with respect to cyclization strategies are reviewed, including solid phase-based cyclization, liquid-phase cyclization, and intramolecular native chemical ligation. Keywords backbone cyclized peptides; chemical synthesis; native chemical ligation 骨架环肽(Backbone cyclized peptides)是线性多肽

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Section: 端芳基酰基肼固定树脂unclassified

Recent Advances in Chemical Synthesis of Backbone Cyclized Peptides

Si¹,

Guo²,

Li³

et al. 2014

Chin. J. Org. Chem.

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Efficient Synthesis and Stereochemical Revision of Coibamide A

Yao

Zhang

et al. 2015

J. Am. Chem. Soc.

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Coibamide A is a highly potent antiproliferative cyclodepsipeptide originally isolated from a Panamanian marine cyanobacterium. Herein we report an efficient solid-phase strategy for assembly of highly N-methylated cyclodepsipeptides, which is invaluable in generating coibamide A derivatives for structure-activity relationship studies. As a consequence of our synthetic studies, two stereochemical assignments of coibamide A were revised and the total synthesis of this natural compound was achieved for the first time.

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Solid-Phase Synthesis and Cyclative Cleavage of Quorum Sensing Depsipeptide Analogues by Acylphenyldiazene Activation

Cited by 2 publications

References 25 publications

Recent Advances in Chemical Synthesis of Backbone Cyclized Peptides

Recent Advances in Chemical Synthesis of Backbone Cyclized Peptides

Efficient Synthesis and Stereochemical Revision of Coibamide A

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Solid-Phase Synthesis and Cyclative Cleavage of Quorum Sensing ­Depsipeptide Analogues by Acylphenyldiazene Activation

Cited by 2 publications

References 25 publications

Recent Advances in Chemical Synthesis of Backbone Cyclized Peptides

Recent Advances in Chemical Synthesis of Backbone Cyclized Peptides

Efficient Synthesis and Stereochemical Revision of Coibamide A

Contact Info

Product

Resources

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Solid-Phase Synthesis and Cyclative Cleavage of Quorum Sensing Depsipeptide Analogues by Acylphenyldiazene Activation