Solution-phase total synthesis of teixobactin

The first solution-phase total synthesis of the cyclic depsipeptide teixobactin is described. Stereoselective construction of L-allo-enduracididine was established, and the protective groups for the peptide coupling reactions and conditions for the assembly of the fragments were also optimised. The...

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Published inOrganic & biomolecular chemistry Vol. 17; no. 5; pp. 1141 - 1153
Main Authors Gao, Bowen, Chen, Sigui, Hou, Yun Nan, Zhao, Yong Juan, Ye, Tao, Xu, Zhengshuang
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 31.01.2019
Royal Society of Chemistry
Subjects
Chemical reactions
Chemistry
Chemistry, Organic
High-performance liquid chromatography
Hydroxyproline
Liquid chromatography
NMR
Nuclear magnetic resonance
Physical Sciences
Science & Technology
Solid phase methods
Solid phase synthesis
Solid phases
Stereoselectivity
IN-VITRO
ANTIBIOTICS
PROTECTING GROUP
ANTIBACTERIAL ACTIVITY
DRUG DISCOVERY
STAPHYLOCOCCUS-AUREUS
DERIVATIVES
EFFICIENT
STEREOCHEMICAL ASSIGNMENT
PEPTIDE
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Summary:The first solution-phase total synthesis of the cyclic depsipeptide teixobactin is described. Stereoselective construction of L-allo-enduracididine was established, and the protective groups for the peptide coupling reactions and conditions for the assembly of the fragments were also optimised. The longest linear sequence for the total synthesis was 20 steps from the known L-cis-4-hydroxyproline derivative and gave a 5.6% overall yield. This solution-phase total synthesis could serve as a complement to the current solidphase synthesis of teixobactin.
Bibliography:ObjectType-Article-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob02803f