TY - JOUR
T1 - Syntheses and biological investigations of kirkamide and oseltamivir hybrid derivatives
AU - Sieber, Simon
AU - Hsiao, Chien Chi
AU - Emmanouilidou, Despina
AU - Debowski, Aleksandra W.
AU - Stubbs, Keith A.
AU - Gademann, Karl
PY - 2020/12/18
Y1 - 2020/12/18
N2 - The C7N-aminocyclitol kirkamide was recently isolated from the plant obligate symbiont Candidatus Burkholderia kirkii and was hypothesized to be beneficial to the plant host due to its cytotoxic activity against insects and arthropods. To study its mechanism of action and inspired by its structural similarity with N-acetylglucosamine (GlcNAc) and oseltamivir, kirkamide-oseltamivir hybrid derivatives were synthesized and investigated for their biological activity. Interestingly, kirkamide analogues were reasonably potent against a known bacterial neuraminidase.
AB - The C7N-aminocyclitol kirkamide was recently isolated from the plant obligate symbiont Candidatus Burkholderia kirkii and was hypothesized to be beneficial to the plant host due to its cytotoxic activity against insects and arthropods. To study its mechanism of action and inspired by its structural similarity with N-acetylglucosamine (GlcNAc) and oseltamivir, kirkamide-oseltamivir hybrid derivatives were synthesized and investigated for their biological activity. Interestingly, kirkamide analogues were reasonably potent against a known bacterial neuraminidase.
KW - Antiviral agents
KW - Glycosidase inhibitors
KW - Natural products
KW - Plant microbe symbiosis
KW - Total synthesis
UR - http://www.scopus.com/inward/record.url?scp=85088142255&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2020.131386
DO - 10.1016/j.tet.2020.131386
M3 - Article
AN - SCOPUS:85088142255
SN - 0040-4020
VL - 76
JO - Tetrahedron
JF - Tetrahedron
IS - 51
M1 - 131386
ER -