Details
| Original language | English |
|---|---|
| Pages (from-to) | 8369-8372 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 21 |
| Issue number | 20 |
| Early online date | 10 Oct 2019 |
| Publication status | Published - 18 Oct 2019 |
Abstract
An improved scalable synthesis of orthogonally functionalized methoxyaspartate, the chiral hinge region element in cystobactamids, is reported. This improvement sets the stage for the total synthesis of four new cystobactamids along with cystobactamid 861-2, whose antibacterial properties are determined and compared. The cyano derivative of cystobactamide 861-2 shows superior antibacterial activity against Gram-negative bacteria to any natural cystobactamide tested so far.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Organic Letters, Vol. 21, No. 20, 18.10.2019, p. 8369-8372.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Scalable Syntheses of Methoxyaspartate and Preparation of the Antibiotic Cystobactamid 861-2 and Highly Potent Derivatives
AU - Moeller, Malte
AU - Norris, Matthew D.
AU - Planke, Therese
AU - Cirnski, Katarina
AU - Herrmann, Jennifer
AU - Müller, Rolf
AU - Kirschning, Andreas
N1 - Funding information: This work was supported by the German Center for Infection Research (DZIF) and the Bundesministerium für Bildung und Forschung (BMBF; project OpCyBac). M.D.N. thanks the Alexander-von Humboldt Foundation for a scholarship.
PY - 2019/10/18
Y1 - 2019/10/18
N2 - An improved scalable synthesis of orthogonally functionalized methoxyaspartate, the chiral hinge region element in cystobactamids, is reported. This improvement sets the stage for the total synthesis of four new cystobactamids along with cystobactamid 861-2, whose antibacterial properties are determined and compared. The cyano derivative of cystobactamide 861-2 shows superior antibacterial activity against Gram-negative bacteria to any natural cystobactamide tested so far.
AB - An improved scalable synthesis of orthogonally functionalized methoxyaspartate, the chiral hinge region element in cystobactamids, is reported. This improvement sets the stage for the total synthesis of four new cystobactamids along with cystobactamid 861-2, whose antibacterial properties are determined and compared. The cyano derivative of cystobactamide 861-2 shows superior antibacterial activity against Gram-negative bacteria to any natural cystobactamide tested so far.
UR - http://www.scopus.com/inward/record.url?scp=85073155969&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.9b03143
DO - 10.1021/acs.orglett.9b03143
M3 - Article
C2 - 31599597
AN - SCOPUS:85073155969
VL - 21
SP - 8369
EP - 8372
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 20
ER -