Details
| Original language | English |
|---|---|
| Pages (from-to) | 564-570 |
| Number of pages | 7 |
| Journal | Beilstein Journal of Organic Chemistry |
| Volume | 12 |
| Publication status | Published - 22 Mar 2016 |
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.
Keywords
- Catalysis, Dehydroamino acids, Hartwig-buchwald reaction, Myxovalargin, Peptides
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
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In: Beilstein Journal of Organic Chemistry, Vol. 12, 22.03.2016, p. 564-570.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Studies on the synthesis of peptides containing dehydrovaline and dehydroisoleucine based on copper-mediated enamide formation
AU - Gille, Franziska
AU - Kirschning, Andreas
PY - 2016/3/22
Y1 - 2016/3/22
N2 - 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.
AB - 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.
KW - Catalysis
KW - Dehydroamino acids
KW - Hartwig-buchwald reaction
KW - Myxovalargin
KW - Peptides
UR - http://www.scopus.com/inward/record.url?scp=84962009797&partnerID=8YFLogxK
U2 - 10.3762/bjoc.12.55
DO - 10.3762/bjoc.12.55
M3 - Article
AN - SCOPUS:84962009797
VL - 12
SP - 564
EP - 570
JO - Beilstein Journal of Organic Chemistry
JF - Beilstein Journal of Organic Chemistry
SN - 1860-5397
ER -