Callynormine A, a New Marine Cyclic Peptide of a Novel Class.

Berer, Nelly; Rudi, Amira; Goldberg, Israel; Benayahu, Yehuda; Kashman, Yoel

doi:10.1002/chin.200448162

Cited by 2 publications

(2 citation statements)

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“…3c). While callynormine contains no N-methyl residues, the crystal structure shows multiple hydrogen bonds both within the ring and between the ring and the tail [43]. The lariat depsipeptide coibamide (MW 1288) also contains 11 amino acids, with 7 residues in the ring and 4 in the tail, and shows low nM cytotoxicity in various human cancer cell lines.…”

Section: Heterodetic Non-polar Cyclic Peptidesmentioning

confidence: 99%

Form and Function in Cyclic Peptide Natural Products: A Pharmacokinetic Perspective

Bockus¹,

McEwen²,

Lokey³

2013

CTMC

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The structural complexity of many natural products sets them apart from common synthetic drugs, allowing them to access a biological target space that lies beyond the enzyme active sites and receptors targeted by conventional small molecule drugs. Naturally occurring cyclic peptides, in particular, exhibit a wide variety of unusual and potent biological activities. Many of these compounds penetrate cells by passive diffusion and some, like the clinically important drug cyclosporine A, are orally bioavailable. These natural products tend to have molecular weights and polar group counts that put them outside the norm based on classic predictors of "drug-likeness". Because of their size and complexity, cyclic peptides occupy a chemical "middle space" in drug discovery that may provide useful scaffolds for modulating more challenging biological targets such as protein-protein interactions and allosteric binding sites. However, the relationship between structure and pharmacokinetic (PK) behavior, especially cell permeability and metabolic clearance, in cyclic peptides has not been studied systematically, and the generality of cyclic peptides as orally bioavailable scaffolds remains an open question. This review focuses on cyclic peptide natural products from a "structure-PK" perspective, outlining what we know and don't know about their properties in the hope of uncovering trends that might be useful in the design of novel "rule-breaking" molecules.

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Section: Heterodetic Non-polar Cyclic Peptidesmentioning

confidence: 99%

Form and Function in Cyclic Peptide Natural Products: A Pharmacokinetic Perspective

Bockus¹,

McEwen²,

Lokey³

2013

CTMC

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“…It is worth to mention, that Callynormine A, is a recently isolated marine metabolite from Kenyan sponges Callyspongia abnormis, appears as a rare N-atom containing heterodetic peptide that has the Z-endiamino group as the key structural element that is proposed to induce conformational rigidity. 14 The role of 1,3-diaminoethenyl structural unit in enzyme sulfatases activity via a serine modification (prokaryotes) or a cysteine modification (eukaryotes and prokaryotes) is studied also. 15 An example of a serine type sulfate is the well characterized bacterial arylsulfatase of Klebsiella pneumoniae.…”

Section: Introductionmentioning

confidence: 99%

Feasibility study on the reaction of 1,4-diazabicyclo[2.2.2]octane (DABCO) with (L-Serine-L-Serine) and (L-Phenylalanine-L-Serine) diketopiperazines

Bhavaraju¹

2016

10.5267/j.ccl

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This paper summarizes the reaction of DABCO with the enol tosylate derivatives made from (L-Ser-L-Ser) and (L-Phe-L-Ser) diketopiperazines (DKP's). The reaction between DABCO and EE-di-tosylate (L-Ser-L-Ser) DKP (2), results in the isomerization of the serine di-tosylate from EE-2 to ZZ-2. This is the first direct example of the utility of DABCO as a reagent demonstrating the successful isomerization in a DKP derivative. The E-enol tosylate of (L-Phe-L-Ser) DKP (4) upon reaction with DABCO provided a unique bis-ylidiene product (5).

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Callynormine A, a New Marine Cyclic Peptide of a Novel Class.

Cited by 2 publications

References 1 publication

Form and Function in Cyclic Peptide Natural Products: A Pharmacokinetic Perspective

Form and Function in Cyclic Peptide Natural Products: A Pharmacokinetic Perspective

Feasibility study on the reaction of 1,4-diazabicyclo[2.2.2]octane (DABCO) with (L-Serine-L-Serine) and (L-Phenylalanine-L-Serine) diketopiperazines

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