An update on new methods to synthesize cyclotetrapeptides

León-Rodríguez, Luis M. De; Weidkamp, Andreas J.; Brimble, Margaret A.

doi:10.1039/c5ob00880h

Cited by 28 publications

(33 citation statements)

References 82 publications

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“…Fungal cyclic peptides mainly include cyclic di-, tri-, tetra-, penta-, hexa-, hepta-, octa-, nona-, and decapeptides. Recent special reviews covering the chemical synthesis [ 10 ], biosynthesis [ 11 , 12 ], as well as developments and applications (i.e., echinocandins, pneumocandins and cyclosporin A) [ 13 , 14 ] of fungal cyclic peptides are available. In this review, we describe the occurrence, biological activities, structures, and potential applications of the fungal cyclic peptides and their analogs, with the exception of cyclodipeptides (called 2,5-diketopiperazines), which were previously reviewed [ 15 ].…”

Section: Introductionmentioning

confidence: 99%

Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides

Wang

Lin

et al. 2017

Molecules

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Cyclic peptides are cyclic compounds formed mainly by the amide bonds between either proteinogenic or non-proteinogenic amino acids. This review highlights the occurrence, structures and biological activities of fungal cyclic peptides (excluding cyclodipeptides, and peptides containing ester bonds in the core ring) reported until August 2017. About 293 cyclic peptides belonging to the groups of cyclic tri-, tetra-, penta-, hexa-, hepta-, octa-, nona-, deca-, undeca-, dodeca-, tetradeca-, and octadecapeptides as well as cyclic peptides containing ether bonds in the core ring have been isolated from fungi. They were mainly isolated from the genera Aspergillus, Penicillium, Fusarium, Acremonium and Amanita. Some of them were screened to have antimicrobial, antiviral, cytotoxic, phytotoxic, insecticidal, nematicidal, immunosuppressive and enzyme-inhibitory activities to show their potential applications. Some fungal cyclic peptides such as the echinocandins, pneumocandins and cyclosporin A have been developed as pharmaceuticals.

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Section: Introductionmentioning

confidence: 99%

Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides

Wang

Lin

et al. 2017

Molecules

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“…Remarkably, the advent of methodologies based on ring‐contraction strategies or the use of pseudoproline amino acid precursors has provided important tools for the synthesis of these highly strained cyclotetrapeptides . Moreover, even for linear peptides containing several turn‐promoting amino acids, the success of cyclization is still sequence dependent . For instance, the cyclo( d Pro‐ d Pro‐Pro‐Pro) peptide can only be obtained upon starting from H‐ d Pro‐Pro‐Pro‐ d Pro‐COOH …”

Section: Introductionmentioning

confidence: 99%

Cyclization of Linear Tetrapeptides Containing N‐Methylated Amino Acids by using 1‐Propanephosphonic Acid Anhydride

Zhang

León-Rodríguez

Lacey³

et al. 2016

Eur J Org Chem

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The cyclization of the linear tetrapeptides sequence H‐NMePhe‐Xaa1‐NMePhe‐Xaa2‐OH (for which Xaa1 = Xaa2 = Ile, Val, or Leu; Xaa1 = Val; Xaa2 = Ile or Leu) by using 1‐propanephosphonic acid anhydride was explored. An unanticipated finding is the cyclization towards cyclotetrapeptide conformers (kinetic products) that were highly prone to hydrolysis and that slowly interconvert into the more stable trans,cis,trans,cis (tctc) conformers (thermodynamic products).

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“…Here, the l ‐ allo ‐enduracididine residue found in teixobactin is replaced with the readily available l ‐Arg . Intramolecular cyclisation, an intrinsically slow process susceptible to side‐reactions such as dimerisation and epimerisation of α‐C on the C‐terminus, is the main synthetic hurdle for all cyclic peptides . Following careful consideration of cyclisation position and coupling reagents, Albericio and his co‐workers accomplished macrolactamisation of the protected peptide in just one day by using PyAOP/OxymaPure/DIEA without side reactions (Figure ).…”

Section: Lipid II Inhibitors As Therapeutic Agentsmentioning

confidence: 99%

New Found Hope for Antibiotic Discovery: Lipid II Inhibitors

Chan

2016

Chemistry A European J

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Abstract:Research into antibacterial agents has recently gathered pace in light of the disturbing crisis of antimicrobial resistance. Development of modern tools offers opportunity of reviving the fallen era of antibacterial discovery through uncovering novel lead compounds that target vital bacterial cell components, such as lipid II. This paper provides a summary of the role of lipid II as well as an overview and insight into the structural features of macrocyclic peptides that inhibit this bacterial cell wall component. The recent discovery of teixobactin, a new class of lipid II inhibitor has generated substantial research interests. As such, the significant progress that has been achieved towards its development as a promising antibacterial agent is discussed.

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An update on new methods to synthesize cyclotetrapeptides

Cited by 28 publications

References 82 publications

Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides

Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides

Cyclization of Linear Tetrapeptides Containing N‐Methylated Amino Acids by using 1‐Propanephosphonic Acid Anhydride

New Found Hope for Antibiotic Discovery: Lipid II Inhibitors

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