Peptide macrocycles featuring a backbone secondary amine: a convenient strategy for the synthesis of lipidated cyclic and bicyclic peptides on solid support.
Identifieur interne : 001631 ( Main/Exploration ); précédent : 001630; suivant : 001632Peptide macrocycles featuring a backbone secondary amine: a convenient strategy for the synthesis of lipidated cyclic and bicyclic peptides on solid support.
Auteurs : Alberto Oddo [Danemark] ; Lena Münzker [Danemark] ; Paul R. Hansen [Danemark]Source :
- Organic letters [ 1523-7052 ] ; 2015.
Descripteurs français
- KwdFr :
- MESH :
English descriptors
- KwdEn :
- Amino Acid Sequence, Antimicrobial Cationic Peptides (chemical synthesis), Antimicrobial Cationic Peptides (chemistry), Molecular Structure, Peptides (chemical synthesis), Peptides (chemistry), Peptides, Cyclic (chemical synthesis), Peptides, Cyclic (chemistry), Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization.
- MESH :
- chemical , chemical synthesis : Antimicrobial Cationic Peptides, Peptides, Peptides, Cyclic.
- chemical , chemistry : Antimicrobial Cationic Peptides, Peptides, Peptides, Cyclic.
- Amino Acid Sequence, Molecular Structure, Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization.
Abstract
A convenient strategy for the on-resin synthesis of macrocyclic peptides (3- to 13-mers) via intramolecular halide substitution by a diamino acid is described. The method is compatible with standard Fmoc/tBu SPPS and affords a tail-to-side-chain macrocyclic peptide featuring an endocyclic secondary amine. This functional group is still reactive toward acylation, allowing for the continuation of the synthesis. An application to the synthesis of lipidated cyclic and bicyclic antimicrobial peptides is presented.
DOI: 10.1021/acs.orglett.5b01026
PubMed: 25923311
Affiliations:
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The method is compatible with standard Fmoc/tBu SPPS and affords a tail-to-side-chain macrocyclic peptide featuring an endocyclic secondary amine. This functional group is still reactive toward acylation, allowing for the continuation of the synthesis. An application to the synthesis of lipidated cyclic and bicyclic antimicrobial peptides is presented. </div></front></TEI><affiliations><list><country><li>Danemark</li></country><region><li>Hovedstaden</li></region><settlement><li>Copenhague</li></settlement></list><tree><country name="Danemark"><region name="Hovedstaden"><name sortKey="Oddo, Alberto" sort="Oddo, Alberto" uniqKey="Oddo A" first="Alberto" last="Oddo">Alberto Oddo</name></region><name sortKey="Hansen, Paul R" sort="Hansen, Paul R" uniqKey="Hansen P" first="Paul R" last="Hansen">Paul R. 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