Abstract
The first synthesis of a naturally occurring tetrapeptide cyclo-(isoleucyl-prolyl-leucyl-alanyl) has been achieved using a solution-phase technique via coupling of dipeptide segments Boc-L-Pro-L-Leu-OH and L-Ala-L-Ile-OMe. Deprotection of the linear tetrapeptide unit and its subsequent cyclization gave a cyclopeptide, identical in all aspects to the naturally occurring compound. Bioactivity results indicated the antifungal and antihelmintic potential of the synthesized peptide against pathogenic dermatophytes and earthworms.
Keywords:
Diginea sp; Halisarca ectofibrosa; biological activity; cyclic tetrapeptide; marine bacteria; natural product synthesis.
MeSH terms
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Animals
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Anthelmintics / chemical synthesis*
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Anthelmintics / chemistry
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Anthelmintics / pharmacology
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Anti-Bacterial Agents / chemical synthesis*
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / pharmacology
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Aquatic Organisms
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Cyclization
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Dipeptides / chemistry
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Microbial Sensitivity Tests
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Oceans and Seas
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Oligopeptides / chemical synthesis*
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Oligopeptides / chemistry
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Oligopeptides / pharmacology
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Parasitic Sensitivity Tests
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Peptides, Cyclic / chemical synthesis*
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Peptides, Cyclic / chemistry
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Peptides, Cyclic / pharmacology
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Porifera / microbiology
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Pseudoalteromonas / chemistry*
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Pseudomonas / chemistry*
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Seaweed / microbiology
Substances
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Anthelmintics
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Anti-Bacterial Agents
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Dipeptides
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Oligopeptides
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Peptides, Cyclic