Efficient synthesis of a side-chain extended diaminodiacid for solid-phase synthesis of peptide disulfide bond mimics

Sun, Shuaishuai; Chen, Junyou; Zhao, Rui; Bierer, Donald; Wang, Jun; Fang, Ge‐Min; Li, Yiming

doi:10.1016/j.tetlet.2019.03.061

Cited by 10 publications

(2 citation statements)

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“…In this context, a new Alloc/allyl protected diaminodiacid containing a five-atom (e. g. CÀ CÀ SÀ CÀ C) bridge (11, Figure 4) has been developed. [18] The usefulness of this diaminodiacid was exemplified in the synthesis of an oxytocin disulfide analogue, the circular dichroism (CD) spectrum of which indicated that its secondary structure was similar to that of native oxytocin.…”

Section: Six-atom or Five-atom Thioether Bridged Diaminodiacidsmentioning

confidence: 99%

A Diaminodiacid (DADA) Strategy for the Development of Disulfide Surrogate Peptides

Bierer

et al. 2020

Chemistry An Asian Journal

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Disulfide bond‐containing peptides are useful molecular scaffolds with diagnostic and therapeutic applications due to their good biological activity and good target selectivity, but their utility is sometimes limited by the lability of the disulfide moiety under reducing conditions and in the presence of disulfide bond isomerase. The development of disulfide surrogates with improved redox stability has been an area of ongoing research; and one possible strategy is based on a diaminodiacid (DADA) moiety, which can be used to synthesize the disulfide bond replacement peptides with precise structures and enhanced stability through automated solid‐phase peptide synthesis (SPPS). This review summarizes recent developments in the DADA‐based SPPS of peptide disulfide surrogates. Some representative applications and structural studies on the DADA‐based disulfide surrogates are described.

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Section: Six-atom or Five-atom Thioether Bridged Diaminodiacidsmentioning

confidence: 99%

A Diaminodiacid (DADA) Strategy for the Development of Disulfide Surrogate Peptides

Bierer

et al. 2020

Chemistry An Asian Journal

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“…Application of combinatorial synthesisGopi et al Beni-Suef University Journal of Basic and Applied Sciences (2020) 9:57 strong interaction of pinholes with the membrane headgroups. Sun et al[35] reported a peptide disulphide bond mimics on the incorporation of diaminodiacids through solid-phase synthesis. It is the most effective method for the synthesis of peptide disulphide bond mimics containing a five-atom thioether (C-C-S-C-C).…”

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An overview of recent progress in modern synthetic approach—combinatorial synthesis

Gopi¹,

Krupamai²,

Sri³

et al. 2020

Beni-Suef Univ J Basic Appl Sci

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Background In recent times, a powerful tool of combinatorial synthesis has been used for the preparation of large chemical entities through a small set up of reactions between different building blocks using solid-phase and solution-phase techniques. This method reduced the time and cost of the drug discovery process substantially. Main text Thousands of compounds are synthesised in a few reactions through combinatorial synthesis instead of getting a few compounds in the traditional method. This method also helps to identify chemical lead of the compounds and optimise them through the biological screening using a high-throughput method. There is no review concerning the recent research finding of combinatorial synthesis. Hence, an attempt had been made on the latest research findings (2002–2020) of newly synthesised compounds using combinatorial synthesis and their biological activities. Conclusion To the best of our knowledge, the current review has completely analysed the importance of combinatorial synthesis and furnished an overview of solid-phase and solution-phase techniques as well as helped mankind by improving higher productivity at low cost, lead identification and optimization and preventing environmental pollution. Graphical abstract

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Chemical Synthesis of Six‐Atom Thioether Bridged Diaminodiacid for Solid‐Phase Synthesis of Peptide Disulfide Bond Mimics

et al. 2020

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Solid phase peptide synthesis (SPPS) strategy based on diaminodiacids had become an effective method for the synthesis of disulfide‐containing polypeptides. At present, it remains necessary to develop a diaminodiacid with more abundant chain structures to study the structure‐activity relationship. In this work, we developed a new type of diaminodiacids containing a six‐atom thioether (C−C‐S−C‐C−C, C−C‐C−S‐C−C) bridge. The key segment protected homo‐homocystine can be efficiently obtained by converting a side chain carboxyl group into a thiol group, which contribute to the facile and efficient synthesis of new diaminodiacid. With this diaminodiacid in hand, we successfully obtained tachyplesin containing new disulfide bond mimic by solid phase peptide synthesis. The tachyplesin analog not only has similar activity as natural counterpart, but also exhibits increased stability under reducing conditions.

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Efficient synthesis of a side-chain extended diaminodiacid for solid-phase synthesis of peptide disulfide bond mimics

Cited by 10 publications

References 46 publications

A Diaminodiacid (DADA) Strategy for the Development of Disulfide Surrogate Peptides

A Diaminodiacid (DADA) Strategy for the Development of Disulfide Surrogate Peptides

An overview of recent progress in modern synthetic approach—combinatorial synthesis

Chemical Synthesis of Six‐Atom Thioether Bridged Diaminodiacid for Solid‐Phase Synthesis of Peptide Disulfide Bond Mimics

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