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Methylene Analogues of Neopetrosiamide as Potential Antimetastatic Agents: Solid-Supported Syntheses Using Diamino Diacids for Pre-Stapling of Peptides with Multiple Disulfides
- Source :
- Organic Letters. 23:9216-9220
- Publication Year :
- 2021
- Publisher :
- American Chemical Society (ACS), 2021.
-
Abstract
- Neopetrosiamide, a 28-residue peptide from Neopetrosia sp., contains three disulfide bonds and hinders mammalian tumor cell invasion. Proper connectivity of disulfide bonds is crucial for activity. Synthetic replacement of single disulfide bridges with methylene bridges gives active analogues. Pre-stapling of one ring enhances the correct formation of the remaining disulfides by reducing isomeric possibilities and possibly initiating the correct 3D fold. Cloning and expression of neopetrosiamide in E. coli affords access to the natural linear peptide.
- Subjects :
- chemistry.chemical_classification
010405 organic chemistry
Stereochemistry
Organic Chemistry
Tumor Cell Invasion
Disulfide bond
Peptide
010402 general chemistry
Ring (chemistry)
01 natural sciences
Biochemistry
3. Good health
0104 chemical sciences
chemistry.chemical_compound
chemistry
Disulfides
Physical and Theoretical Chemistry
Methylene
Subjects
Details
- ISSN :
- 15237052 and 15237060
- Volume :
- 23
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi.dedup.....1b20bcbf5eb3fb6a70c391f827d1e154