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Total Synthesis of the Highly N-Methylated Acetylene-Containing Anticancer Peptide Jahanyne.

07:00 EST 16th January 2018 | BioPortfolio

Summary of "Total Synthesis of the Highly N-Methylated Acetylene-Containing Anticancer Peptide Jahanyne."

The first total synthesis of the highly N-methylated acetylene-containing lipopeptide jahanyne, an apoptosis-inducing natural product from marine cyanobacteria, is reported. A late-stage solution-phase coupling enabled introduction of the C-terminal ketone pyrrolidine moiety. A modified Fmoc solid-phase synthesis strategy was adopted to effectively couple multiple sterically hindered N-methylated amino acids while suppressing epimerization. The total synthesis has enabled confirmation of the proposed absolute configuration of natural jahanyne.

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Name: Organic letters
ISSN: 1523-7052
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Medical and Biotech [MESH] Definitions

The simplest two carbon alkyne with the formula HCCH.

A methylated nucleotide base found in eukaryotic DNA. In ANIMALS, the DNA METHYLATION of CYTOSINE to form 5-methylcytosine is found primarily in the palindromic sequence CpG. In PLANTS, the methylated sequence is CpNpGp, where N can be any base.

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.

A highly basic, 28 amino acid neuropeptide released from intestinal mucosa. It has a wide range of biological actions affecting the cardiovascular, gastrointestinal, and respiratory systems and is neuroprotective. It binds special receptors (RECEPTORS, VASOACTIVE INTESTINAL PEPTIDE).

A protein domain of about 70 amino acids in length that folds into a sandwich structure consisting of a beta sheet, alpha helix, and C-terminal hairpin loop which forms a hydrophobic methylated-DNA binding patch. It binds to methylated CPG ISLANDS in eukaryotes and occurs with other DNA and CHROMATIN binding domains such as AT-HOOK MOTIFS in eukaryotic DNA BINDING PROTEINS.

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