ArticleOrganic & biomolecular chemistry2009
Solid-phase synthesis of cyclic peptide chitinase inhibitors: SAR of the argifin scaffold.
Article in Organic & biomolecular chemistry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
7 citing papers in PubMed, 32 citations in OpenAlex.
- Total Synthesis and Structural Revision of Rhabdobranin Reveals a Cryptic Gram-Negative Antibiotic.Journal of the American Chemical Society · 2026Article
- Total synthesis of the putative structure of the proposed Banyasin A.Frontiers in chemistry · 2015Article
- Potent family-18 chitinase inhibitors: x-ray structures, affinities, and binding mechanisms.The Journal of biological chemistry · 2011Article
- Two-Steps Hantzsch Based Macrocyclization Approach for the Synthesis of Thiazole Containing Cyclopeptides.The Journal of organic chemistry · 2010Article
- Parallel synthesis and anti-inflammatory activity of cyclic peptides cyclosquamosin D and Met-cherimolacyclopeptide B and their analogs.Bioorganic & medicinal chemistry letters · 2010Article
- On resin amino acid side chain attachment strategy for the head to tail synthesis of new glutamine containing gramicidin-S analogs and their antimicrobial activity.Bioorganic & medicinal chemistry letters · 2010Article
- Recent development of two chitinase inhibitors, Argifin and Argadin, produced by soil microorganisms.Proceedings of the Japan Academy. Series B, Physical and biological sciences · 2010Review
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
Abstract
A new, highly efficient, all-solid-phase synthesis of argifin, a natural product cyclic pentapeptide chitinase inhibitor, is reported. The synthesis features attachment of an orthogonally protected Asp residue to the solid support and assembly of the linear peptide chain by Fmoc SPPS prior to cyclisation and side-chain manipulation on-resin. Introduction of the key N-methyl carbamoyl-substituted Arg side chain is achieved via derivatisation of a selectively protected Orn residue, prior to cleavage from the resin and side-chain deprotection. A severe aspartimide side-reaction observed upon final deprotection is circumvented by the use of a novel aqueous acidolysis procedure. The flexibility of the synthesis is demonstrated by the preparation of a series of argifin analogues designed from the X-ray structure of the natural product in complex with a representative family 18 chitinase.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.