Cargando…
First total synthesis of versicotide A, B and C
The syntheses of versicotides A–C, natural products containing anthranilic acid and NMe-Ala, were achieved by solid phase peptide synthesis on 2-chlorotrityl resin followed by solution phase macrocyclization. Using an oxyma additive, the difficult coupling reactions to the deactivated aromatic amine...
Autores principales: | , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2020
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9058379/ https://www.ncbi.nlm.nih.gov/pubmed/35519702 http://dx.doi.org/10.1039/d0ra09635k |
_version_ | 1784698101610577920 |
---|---|
author | Posada, Laura Davyt, Danilo Serra, Gloria |
author_facet | Posada, Laura Davyt, Danilo Serra, Gloria |
author_sort | Posada, Laura |
collection | PubMed |
description | The syntheses of versicotides A–C, natural products containing anthranilic acid and NMe-Ala, were achieved by solid phase peptide synthesis on 2-chlorotrityl resin followed by solution phase macrocyclization. Using an oxyma additive, the difficult coupling reactions to the deactivated aromatic amine of o-aminobenzoic acid, were performed in high yield, avoiding anthranilic rearrangements or side reactions. |
format | Online Article Text |
id | pubmed-9058379 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-90583792022-05-04 First total synthesis of versicotide A, B and C Posada, Laura Davyt, Danilo Serra, Gloria RSC Adv Chemistry The syntheses of versicotides A–C, natural products containing anthranilic acid and NMe-Ala, were achieved by solid phase peptide synthesis on 2-chlorotrityl resin followed by solution phase macrocyclization. Using an oxyma additive, the difficult coupling reactions to the deactivated aromatic amine of o-aminobenzoic acid, were performed in high yield, avoiding anthranilic rearrangements or side reactions. The Royal Society of Chemistry 2020-12-09 /pmc/articles/PMC9058379/ /pubmed/35519702 http://dx.doi.org/10.1039/d0ra09635k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Posada, Laura Davyt, Danilo Serra, Gloria First total synthesis of versicotide A, B and C |
title | First total synthesis of versicotide A, B and C |
title_full | First total synthesis of versicotide A, B and C |
title_fullStr | First total synthesis of versicotide A, B and C |
title_full_unstemmed | First total synthesis of versicotide A, B and C |
title_short | First total synthesis of versicotide A, B and C |
title_sort | first total synthesis of versicotide a, b and c |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9058379/ https://www.ncbi.nlm.nih.gov/pubmed/35519702 http://dx.doi.org/10.1039/d0ra09635k |
work_keys_str_mv | AT posadalaura firsttotalsynthesisofversicotideabandc AT davytdanilo firsttotalsynthesisofversicotideabandc AT serragloria firsttotalsynthesisofversicotideabandc |