dc.identifier.uri |
http://dx.doi.org/10.15488/664 |
|
dc.identifier.uri |
http://www.repo.uni-hannover.de/handle/123456789/688 |
|
dc.contributor.author |
Gille, Franziska
|
|
dc.contributor.author |
Kirschning, Andreas
|
|
dc.date.accessioned |
2016-11-04T10:43:07Z |
|
dc.date.available |
2016-11-04T10:43:07Z |
|
dc.date.issued |
2016 |
|
dc.identifier.citation |
Gille, Franziska; Kirschning, Andreas: Studies on the synthesis of peptides containing dehydrovaline and dehydroisoleucine based on copper-mediated enamide formation. In: Beilstein Journal of Organic Chemistry 12 (2016), S. 564-570. DOI: http://dx.doi.org/10.3762/bjoc.12.55 |
|
dc.description.abstract |
The preparation of peptide fragments containing dehydrovaline and dehydroisoleucine moieties present in the antibiotic myxovalargin is reported. Peptide formation is based on a copper-mediated C-N cross-coupling protocol between an acyl amide and a peptidic vinyl iodide. The presence of a neighboring arginine in the vinyl iodide posed a challenge with respect to the choice of the protecting group and the reaction conditions. It was found that ornithine - a suitable precursor - is better suited than arginine for achieving good yields for the C-N cross-coupling reaction. The optimized conditions were utilized for the synthesis of peptides 32, 33, 39 and 40 containing a neighboring ornithine as well as for the tripeptide 44 containing dehydroisoleucine with the correct stereochemistry. |
eng |
dc.language.iso |
eng |
|
dc.publisher |
Frankfurt am Main : Beilstein-Institut Zur Förderung der Chemischen Wissenschaften |
|
dc.relation.ispartofseries |
Beilstein Journal of Organic Chemistry 12 (2016) |
|
dc.rights |
CC BY 2.0 Unported |
|
dc.rights.uri |
http://creativecommons.org/licenses/by/2.0 |
|
dc.subject |
Catalysis |
eng |
dc.subject |
Dehydroamino acids |
eng |
dc.subject |
Hartwig-buchwald reaction |
eng |
dc.subject |
Myxovalargin |
eng |
dc.subject |
Peptides |
eng |
dc.subject.ddc |
500 | Naturwissenschaften
|
ger |
dc.subject.ddc |
540 | Chemie
|
ger |
dc.title |
Studies on the synthesis of peptides containing dehydrovaline and dehydroisoleucine based on copper-mediated enamide formation |
eng |
dc.type |
Article |
|
dc.type |
Text |
|
dc.relation.issn |
1860-5397 |
|
dc.relation.doi |
http://dx.doi.org/10.3762/bjoc.12.55 |
|
dc.bibliographicCitation.volume |
12 |
|
dc.bibliographicCitation.firstPage |
564 |
|
dc.bibliographicCitation.lastPage |
570 |
|
dc.description.version |
publishedVersion |
|
tib.accessRights |
frei zug�nglich |
|