Claims
- 1. A chemical compound having the structure: ##STR11## wherein R.sub.1 and R.sub.2 are the same or different and are selected from the group consisting of --C(O)NHR.sub.3, --(CH.sub.2).sub.n O-saccharides, --(CH.sub.2).sub.n O-DNA intercalators, --(CH.sub.2).sub.n O-DNA minor groove binders, --(CH.sub.2).sub.n O-DNA binding proteins, --(CH.sub.2).sub.n O-DNA fragments, --(CH.sub.2).sub.n O-RNA fragments, or --(CH.sub.2).sub.n O-monoclonal antibodies, where n=1-10, preferably 1-5 and R.sub.3 is selected from the group consisting of saccharides, DNA intercalators, DNA minor groove binders, DNA binding proteins, DNA fragments, RNA fragments, or monoclonal antibodies.
- 2. The chemical compound of claim 1 wherein the hydrogens on the bridgehead carbons are in the cis configuration.
- 3. The chemical compound of claim 1 wherein the hydrogens on the bridgehead carbons are in the trans configuration.
- 4. The chemical compound of claim 1 wherein either R.sub.1 or R.sub.2, or both of them, is --CH.sub.2 O-glucose.
- 5. The chemical compound of claim 1 wherein either R.sub.1 or R.sub.2, or both of them, is --CH.sub.2 O-glucose and the hydrogens on the bridgehead carbons are in the cis configuration.
- 6. A method of cleaving DNA comprising contacting the DNA molecule to be cleaved with the compound of claim 1.
- 7. The method of claim 6, wherein R.sub.1 and R.sub.2 of the compound of claim 1 are --CH.sub.2 O-glucose.
- 8. A method of preparing the chemical compound of claim 1 comprising:
- a) cleaving the carbon-carbon double bond of a chemical compound having the structure: ##STR12## where R.sub.1 and R.sub.2 are defined as in claim 1, to form two terminal aldehyde groups at the points of cleavage,
- b) reacting the dialdehyde product of step (a) with carbon tetrabromide to produce two terminal dibromo olefin groups,
- c) converting the terminal olefin groups of the product of step (b) to acetylenic groups bearing terminal dihalomethyl groups,
- d) cyclizing the diacetylenic product of step (c) with a sulfur-containing compound to yield an eleven-membered cyclic sulfide,
- e) converting the cyclic sulfide of step (d) to an eleven-membered cyclic alpha-halo sulfone, and
- f) treating the alpha-halo sulfone of step (e) with a base to produce the chemical compound of claim 1.
- 9. A method of preparing the chemical compound of claim 1 comprising:
- a) reacting a chemical compound having the structure: ##STR13## where R.sub.1 and R.sub.2 are defined as in claim 1, with ozone and then trimethyl phosphite to effect the cleavage of the carbon-carbon double bond and the formation of two aldehyde groups,
- b) reacting the dialdehyde product of step (a) with carbon tetrabromide and triphenylphosphine to add one carbon to each of the aldehydes and to produce terminal dibromo olefin groups,
- c) converting the terminal olefin groups of the product of step (b) to acetylenic groups bearing terminal dihalomethyl groups by treating the olefinic product of step (b) with n-butyllithium and methyl chloroformate, then diisobutylaluminum hydride, then trimethyl phosphite and carbon tetrahalide,
- d) reacting the diacetylenic product of step c) with sodium sulfide nonahydrate to yield an eleven membered cyclic sulfide,
- e) contacting the cyclic sulfide of step d) with 3-chloroperbenzoic acid, then sulfuryl chloride and pyridine, then 3-chloroperbenzoic acid to produce an eleven membered cyclic alpha-chloro sulfone, and
- f) contacting the alpha-chloro sulfone of step (e) with methyllithium to produce the compound of claim 1.
- 10. A method of preparing the chemical compounds of claim 1 comprising reacting a cyclic alpha-halo sulfone of the structure: ##STR14## wherein X is F, Cl, Br, or I, with a base.
- 11. The method of claim 10, wherein X is Cl.
- 12. The method of claim 10, wherein the base is methyllithium.
- 13. The method of claim 10 wherein X is Cl and the base is methyllithium.
- 14. A method of preparing the compound of claim 1 comprising reacting a compound of structure: ##STR15## with 3-chloroperbenzoic acid, then sulfuryl chloride, then 3-chloroperbenzoic acid to produce a compound of structure: ##STR16## and then treating that compound with a base.
- 15. The method of claim 14 wherein the base is methyllithium.
Parent Case Info
This is a division of application Ser. No. 214,019, filed Jun. 30, 1988, now U.S. Pat. No. 5,097,062.
GOVERNMENT SUPPORT
Portions of this invention were supported by a grant from the National Science Foundation.
Non-Patent Literature Citations (3)
Entry |
Anon., Synform, 8(2), 90-112, 1990. |
Singh, R. et al., Tetrahedron Lett., 31(2) 185-8, 1990. |
Nicolaou, K. C. et al., J. Am. Chem. Soc. 110(21) 7247-48, 1988. |
Divisions (1)
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Number |
Date |
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214019 |
Jun 1988 |
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