Details
| Original language | English |
|---|---|
| Pages (from-to) | 1324-1333 |
| Number of pages | 10 |
| Journal | Chemistry - A European Journal |
| Volume | 4 |
| Issue number | 7 |
| Publication status | Published - Jul 1998 |
| Externally published | Yes |
Abstract
The naturally occurring ten-membered lactones decarestrictine B (4) and D (5), which lower cholesterol levels, were glycosylated with deoxygenated 2-selenoglycosyl acetates 7a, 7b, and glycal 10 (obtained from D-glucose), and glycal 13 (obtained from L-rhamnose). Depending on the glycosylation method employed, the triol decarestrictine D was glycosylated with a high degree of regioselectivity. A set of hybrid structures were yielded by O-deblocking and in most cases reductive removal of a halogen or a phenylselenyl group from C-2 of the glycosides 14a-f, 20a, 20b, and 24. These hybrids were subjected to preliminary biological tests in which the novel glycoconjugates 15d and 15e displayed DNA-binding properties.
Keywords
- Antibiotics, DNA recognition, Glycosides, Glycosylations, Macrocycles
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Chemistry - A European Journal, Vol. 4, No. 7, 07.1998, p. 1324-1333.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - First glycosylation of decarestrictine B and D
T2 - A route to hybrid antibiotics
AU - Dräger, Gerald
AU - Garming, Alfons
AU - Maul, Corinna
AU - Noltemeyer, Mathias
AU - Thiericke, Ralf
AU - Zerlin, Marion
AU - Kirschning, Andreas
PY - 1998/7
Y1 - 1998/7
N2 - The naturally occurring ten-membered lactones decarestrictine B (4) and D (5), which lower cholesterol levels, were glycosylated with deoxygenated 2-selenoglycosyl acetates 7a, 7b, and glycal 10 (obtained from D-glucose), and glycal 13 (obtained from L-rhamnose). Depending on the glycosylation method employed, the triol decarestrictine D was glycosylated with a high degree of regioselectivity. A set of hybrid structures were yielded by O-deblocking and in most cases reductive removal of a halogen or a phenylselenyl group from C-2 of the glycosides 14a-f, 20a, 20b, and 24. These hybrids were subjected to preliminary biological tests in which the novel glycoconjugates 15d and 15e displayed DNA-binding properties.
AB - The naturally occurring ten-membered lactones decarestrictine B (4) and D (5), which lower cholesterol levels, were glycosylated with deoxygenated 2-selenoglycosyl acetates 7a, 7b, and glycal 10 (obtained from D-glucose), and glycal 13 (obtained from L-rhamnose). Depending on the glycosylation method employed, the triol decarestrictine D was glycosylated with a high degree of regioselectivity. A set of hybrid structures were yielded by O-deblocking and in most cases reductive removal of a halogen or a phenylselenyl group from C-2 of the glycosides 14a-f, 20a, 20b, and 24. These hybrids were subjected to preliminary biological tests in which the novel glycoconjugates 15d and 15e displayed DNA-binding properties.
KW - Antibiotics
KW - DNA recognition
KW - Glycosides
KW - Glycosylations
KW - Macrocycles
UR - http://www.scopus.com/inward/record.url?scp=0032127049&partnerID=8YFLogxK
U2 - 10.1002/(SICI)1521-3765(19980710)4:7<1324::AID-CHEM1324>3.0.CO;2-6
DO - 10.1002/(SICI)1521-3765(19980710)4:7<1324::AID-CHEM1324>3.0.CO;2-6
M3 - Article
AN - SCOPUS:0032127049
VL - 4
SP - 1324
EP - 1333
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 7
ER -