Solid-Phase Total Synthesis of Dehydrotryptophan-Bearing Cyclic Peptides Tunicyclin B, Sclerotide A, CDA3a, and CDA4a using a Protected β-Hydroxytryptophan Building Block
| Autor: | Scott D. Taylor, Matthew Diamandas, Ryan Moreira |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
Fluorenes Molecular Structure 010405 organic chemistry Stereochemistry Organic Chemistry Fmoc chemistry Total synthesis Alcohol 010402 general chemistry Cleavage (embryo) Block (periodic table) 01 natural sciences Biochemistry Peptides Cyclic Cyclic peptide 0104 chemical sciences 5-Hydroxytryptophan chemistry.chemical_compound chemistry Yield (chemistry) Phase (matter) Physical and Theoretical Chemistry Amino Acids Solid-Phase Synthesis Techniques |
| Zdroj: | Organic letters. 23(8) |
| ISSN: | 1523-7052 |
| Popis: | A new approach to the synthesis of Z-dehydrotryptophan (ΔTrp) peptides is described. This approach uses Fmoc-β-HOTrp(Boc)(TBS)-OH as a building block, which is readily prepared in high yield and incorporated into peptides using solid-phase Fmoc chemistry. The tert-butyldimethylsilyl-protected indolic alcohol is eliminated during global deprotection/resin cleavage to give ΔTrp peptides exclusively as the thermodynamically favored Z isomer. This approach was applied to the solid-phase synthesis of tunicyclin B, sclerotide A, CDA3a, and CDA4a. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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