Macrocyclic N-Methylated Cyclic Peptides and Depsipeptides

Maharani, Rani; Sleebs, Brad E.; Hughes, Andrew B.

doi:10.1016/b978-0-444-63460-3.00004-3

Cited by 6 publications

(9 citation statements)

References 242 publications

(466 reference statements)

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“…α-Hydroxy acids are a class of compounds that are always present in depsipeptides (Luesch et al 2002;Sasaki et al 1992;Suzuki et al 1970;Tomoda et al 1992). Reviews on the depsipeptides have been discussed in several articles including their interesting biological activity (Andavan & Lemmens-Gruber 2010;Maharani et al 2015). Aureobasidin A and petriellin A are two cyclodepsipeptides that contain hydroxy acids in their structures (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of α-Hydroxyisovaleric acid (Hiv) and α-Acetyloxyisovaleric Acid (Ac-Hiv), Precursors of Aureobasidin B, with Improved Yield

Maharani¹,

Rahim

Rizqullah

et al. 2018

Chim. Nat. Acta

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α-Hydroxyisovaleric acid (Ac-Hiv) and α-acetyloxyisovaleric acid (Ac-Hiv) have been successfully synthesized through a diazotisation of amino acid using sodium nitrite with the catalyst of sulfuric acid and acetic acid, respectively. In the synthesis of Hiv, Zubia et al. (2005) mentioned that 3 equivalents of sodium nitrite for the reaction gave the hydroxy acid with a good yield. However, Cohen-Arazi et al. (2008) described that 6 equivalents of sodium nitrite resulted the highest yield. In present study, a variation of equivalents of sodium nitrite (3, 4, 5, 6 eq.) were trialed for the same method of synthesis. Through several experiments, we found that 6 equivalents of sodium nitrite were the best portion among all. This finding was applied into the synthesis of protected Hiv (Ac-Hiv) that was previously reported by Maharani et al. (2017) giving 63% yield when 3 equivalent of sodium nitrite was employed. By increasing the equivalent of sodium nitrite into 6 equivalents, the Ac-Hiv can be synthesized with an improved yield (71%).

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Section: Introductionmentioning

confidence: 99%

Synthesis of α-Hydroxyisovaleric acid (Hiv) and α-Acetyloxyisovaleric Acid (Ac-Hiv), Precursors of Aureobasidin B, with Improved Yield

Maharani¹,

Rahim

Rizqullah

et al. 2018

Chim. Nat. Acta

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“…This is indicative of the simultaneous presence of cis and trans amides along the backbone. According to literature, for pe side chains, 1 H NMR resonances between 5.5 and 6 ppm are associated with benzylic protons on cis amides and those around 5 ppm are from benzylic protons on trans amides. 17 The average amide cis/trans ratio was estimated to 75 : 25 in CD 3 CN (Fig.…”

Section: Experimental Designmentioning

confidence: 99%

“…1 Their biological properties are often associated to their binding of metal cations. For example, the destruxins are a family of cyclohexadepsipeptides capable of modifying various Ca 2+ -dependent processes.…”

Section: Introductionmentioning

confidence: 99%

Selective complexation of divalent cations by a cyclic α,β-peptoid hexamer: a spectroscopic and computational study

et al. 2016

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“…Backbone N-methylation was long thought to be an exclusive modification of non-ribosomally produced peptides 227 exemplified by the immunosuppressant cyclosporin A (Dreyfuss et al 1976), the antibiotic actinomycin S 228 (Hollstein 1974) and several depsipeptides (Maharani et al 2015). In all these cases, the methylation of the from the ribosomally produced precursor phomA in P. leptostromiformis (Ding et al 2016).…”

mentioning

confidence: 99%

Discovery of novel fungal RiPP biosynthetic pathways and their application for the development of peptide therapeutics

Vogt

Künzler

2019

Appl Microbiol Biotechnol

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Bioactive peptide natural products are an important source of therapeutics. Prominent examples are the 19 antibiotic penicillin and the immunosuppressant cyclosporine which are both produced by fungi and have 20 revolutionized modern medicine. Peptide biosynthesis can occur either non-ribosomally via large enzymes 21 referred to as non-ribosomal peptide synthetases (NRPS) or ribosomally. Ribosomal peptides are synthesized as 22 part of a larger precursor peptide where they are posttranslationally modified and subsequently proteolytically 23 released. Such peptide natural products are referred to as ribosomally synthesized and posttranslationallly 24 modified peptides (RiPPs). Their biosynthetic pathways have recently received a lot of attention, both from a 25 basic and applied research point of view, due to the discoveries of several novel posttranslational modifications 26 of the peptide backbone. Some of these modifications were so far only known from NRPSs and significantly 27 increase the chemical space covered by this class of peptide natural products. Latter feature, in combination with 28 the promiscuity of the modifying enzymes and the genetic encoding of the peptide sequence, makes RiPP 29 biosynthetic pathways attractive for synthetic biology approaches to identify novel peptide therapeutics via 30 screening of de novo generated peptide libraries and, thus, exploit bioactive peptide natural products beyond 31 their direct use as therapeutics. This review focuses on the recent discovery and characterization of novel RiPP 32 biosynthetic pathways in fungi and their possible application for the development of novel peptide therapeutics. 33 34 38 Meanwhile, the search for novel natural products with pharmacological activities continues. High-throughput 39 screens using molecular and cellular bioassays allow the evaluation of large numbers of natural products and 40 synthetically generated compound libraries for bioactivities of interest. Statistical analysis of the 41 complementarity of natural products and synthetic compounds showed that 40% of chemical scaffolds of natural 42 products are absent in synthetic compound libraries (Henkel et al. 1999), demonstrating that the biomedical 43 relevance of natural products lies in their wide range of structural diversity and complexity. Thus, natural 44 products continue to play a significant role in drug development. From the 1940s to 2014, 40% of small molecules 45 approved for cancer treatment were natural products or derivatives thereof (Newman and Cragg 2016). Plants 46 and microorganisms are the main sources of bioactive natural products (Dias et al. 2012). The vast dimension of 47 'microbial dark matter' suggested by genomic microbiome studies promises an enormous variety of bioactive48natural products yet to be discovered (Solden et al. 2016). This is also true for fungi where it is assumed that only 49 about one-twentieth of all existing fungi have been described and an even smaller fraction has been cultured 50 successfully in the lab (Jiang and An 2000...

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Macrocyclic N-Methylated Cyclic Peptides and Depsipeptides

Cited by 6 publications

References 242 publications

Synthesis of α-Hydroxyisovaleric acid (Hiv) and α-Acetyloxyisovaleric Acid (Ac-Hiv), Precursors of Aureobasidin B, with Improved Yield

Synthesis of α-Hydroxyisovaleric acid (Hiv) and α-Acetyloxyisovaleric Acid (Ac-Hiv), Precursors of Aureobasidin B, with Improved Yield

Selective complexation of divalent cations by a cyclic α,β-peptoid hexamer: a spectroscopic and computational study

Discovery of novel fungal RiPP biosynthetic pathways and their application for the development of peptide therapeutics

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