Details
| Original language | English |
|---|---|
| Pages (from-to) | 3505-3521 |
| Number of pages | 17 |
| Journal | Tetrahedron |
| Volume | 60 |
| Issue number | 15 |
| Publication status | Published - 17 Mar 2004 |
Abstract
The preparation of linear 1,4-butanediol-linked oligodeoxysugars 50-53, 58 and 60 is described which are potential binders to polynucleotides. Various aminodeoxymonosaccharides 9, 13-18, 30, 31 and 40-42 which are either allylated at the anomeric center or at C4 were subjected to the metathesis olefination protocol. Depending on the position of allylation E/Z-mixtures of C 2-symmetric head-to-head or tail-to-tail homodimers were formed. Among them, saccharides 13, 30, 31 and 40 were transformed into the corresponding 1,4-butanediol linked disaccharides 50-53 by catalytic hydrogenation of the central olefinic double bond and exhaustive deprotection. In order to target extended spacer-linked neooligosaccharides homodimeric aminoglycoside 37 was bisallylated and subjected to cross metathesis conditions using methyl 4-O-allyl daunosamide 40 as reaction partner which yielded two desired trimeric and tetrameric linearly spacer-linked daunosamine derivatives. After hydrogenation and deprotection two additional probes 58 and 60 for nucleic acid binding studies were at hand.
Keywords
- Aminoglycosides, Carbohydrates, Metathesis, Olefination, Rearrangement, RNA-binding
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Pharmacology, Toxicology and Pharmaceutics(all)
- Drug Discovery
- Chemistry(all)
- Organic Chemistry
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In: Tetrahedron, Vol. 60, No. 15, 17.03.2004, p. 3505-3521.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Synthesis of extended spacer-linked neooligodeoxysaccharides by metathesis olefination and evaluation of their RNA-binding properties
AU - Kirschning, Andreas
AU - Chen, Guang Wu
AU - Jaunzems, Janis
AU - Jesberger, Martin
AU - Kalesse, Markus
AU - Lindner, Meike
N1 - Funding information: This work was supported by the Deutsche Forschungsgemeinschaft (SFB 416, project B2 and KA 913/6-1) and by the Fonds der Chemischen Industrie. This project is part of the joint initiative ‘Biologisch aktive Naturstoffe-Synthetische Diversität’ at the University of Hannover. We thank Dmitri Kashin for preparative assistance.
PY - 2004/3/17
Y1 - 2004/3/17
N2 - The preparation of linear 1,4-butanediol-linked oligodeoxysugars 50-53, 58 and 60 is described which are potential binders to polynucleotides. Various aminodeoxymonosaccharides 9, 13-18, 30, 31 and 40-42 which are either allylated at the anomeric center or at C4 were subjected to the metathesis olefination protocol. Depending on the position of allylation E/Z-mixtures of C 2-symmetric head-to-head or tail-to-tail homodimers were formed. Among them, saccharides 13, 30, 31 and 40 were transformed into the corresponding 1,4-butanediol linked disaccharides 50-53 by catalytic hydrogenation of the central olefinic double bond and exhaustive deprotection. In order to target extended spacer-linked neooligosaccharides homodimeric aminoglycoside 37 was bisallylated and subjected to cross metathesis conditions using methyl 4-O-allyl daunosamide 40 as reaction partner which yielded two desired trimeric and tetrameric linearly spacer-linked daunosamine derivatives. After hydrogenation and deprotection two additional probes 58 and 60 for nucleic acid binding studies were at hand.
AB - The preparation of linear 1,4-butanediol-linked oligodeoxysugars 50-53, 58 and 60 is described which are potential binders to polynucleotides. Various aminodeoxymonosaccharides 9, 13-18, 30, 31 and 40-42 which are either allylated at the anomeric center or at C4 were subjected to the metathesis olefination protocol. Depending on the position of allylation E/Z-mixtures of C 2-symmetric head-to-head or tail-to-tail homodimers were formed. Among them, saccharides 13, 30, 31 and 40 were transformed into the corresponding 1,4-butanediol linked disaccharides 50-53 by catalytic hydrogenation of the central olefinic double bond and exhaustive deprotection. In order to target extended spacer-linked neooligosaccharides homodimeric aminoglycoside 37 was bisallylated and subjected to cross metathesis conditions using methyl 4-O-allyl daunosamide 40 as reaction partner which yielded two desired trimeric and tetrameric linearly spacer-linked daunosamine derivatives. After hydrogenation and deprotection two additional probes 58 and 60 for nucleic acid binding studies were at hand.
KW - Aminoglycosides
KW - Carbohydrates
KW - Metathesis
KW - Olefination
KW - Rearrangement
KW - RNA-binding
UR - http://www.scopus.com/inward/record.url?scp=1642410821&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2004.02.013
DO - 10.1016/j.tet.2004.02.013
M3 - Article
AN - SCOPUS:1642410821
VL - 60
SP - 3505
EP - 3521
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 15
ER -