Claims
- 1. A phosphine-borane complex of formula:
- 2. The complex of claim 1 wherein PR is an acyl group.
- 3. The complex of claim 1 wherein PR is a —CO—R5 group where R5 is hydrogen or an optionally substituted alkyl or aryl group.
- 4. The complex of claim 1 wherein R and R′ are optionally substituted alkyl groups.
- 5. The complex of claim 1 wherein R and R′ are optionally substituted aryl groups.
- 6. The complex of claim 1 wherein R″ are all the same and are selected from H or a small alkyl group.
- 7. The complex of claim 1 R2 and R3 are H or small alkyl groups.
- 8. The complex of claim 1 wherein R and R′ are ethyl groups.
- 9. A phosphine-borane complex of formula:
- 10. The complex of claim 9 wherein the AA group is an amino acid or a fully or partially protected derivative thereof.
- 11. The complex of claim 9 wherein the AA group is a peptide or a fully or partially protected derivative thereof.
- 12. The complex of claim 9 wherein n is 1, 2 or 3.
- 13. The complex of claim 9 wherein AA is selected from the group consisting of glycine, alanine, valine, leucine, isoleucine, phenylalanine, serine, methionine, proline, tyrosine, tryptophan, lysine, arginine, histidine, asparate, glutamate, asparagine, glutamine, cysteine, methionine, hydroxyproline, γ-carboxyglutamate, O-phosphoserine, ornithine, homoarginine and various protected derivatives thereof.
- 14. The complex of claim 9 wherein AA is a naturally-occurring or synthetically prepared amino acid.
- 15. The complex of claim 9 wherein R and R′ are optionally substituted alkyl, alkoxy or aryl groups.
- 16. The complex of claim 9 wherein R and R′ are ethyl groups.
- 17. The complex of claim 9 wherein R2, R3 are H.
- 18. The complex of claim 9 R″ are all H or all small alky groups.
- 19. A method for synthesis of a phosphinothiol reagent which comprises the steps of:
(a) reacting a phosphine-borane complex of formula: 25with an alkylating agent of formula: 26to form a phosphine-borane complex of formula: 27(b) disrupting the phoshine-borane product of step a; and (c) and deprotecting the product of step b to form a phosphinothiol reagent wherein:
PR is a protecting group; X is a leaving group; R and R′, independently of one another, are optionally substituted alkyl, aryl or alkoxy groups where R and R′ may be the same or different groups and R and R′ may be covalently linked to each other; R″, independently of other R″ in the compound, can be H, an optionally substituted alkyl or aryl group where all three of R″ may be the same or each may be different, and any two or three of R″ may be covalently linked to each other; and R2 and R3, independently of one another, can be selected from H, or optionally substituted alkyl or aryl groups, where R2 and R3 may be covalently linked to each other.
- 20. A method for forming an amide bond which comprises the step of reacting a an azide with a phoshine-borane complex of formula:
- 21. The method of claim 20 wherein R and R′ are optionally substituted alkyl groups.
- 22. The method of claim 20 wherein R and R′ are ethyl groups.
- 23. The method of claim 20 wherein n is 1 and AA is an amino acid.
- 24. The method of claim 20 wherein AA is a peptide or a protein.
- 25. The method of claim 24 wherein n is 1.
- 26. The method of claim 20 wherein the azide is an azide of an amino acid, a peptide or a protein.
- 27. The method of claim 20 wherein the azide is an azide of a carbohydrate.
- 28. The method of claim 20 wherein the azide is an azide of a saccharide which may be a mono, di or tri saccharide.
- 29. The method of claim 20 wherein R″ are all H or are all small alkyl groups.
- 30. The method of claim 20 wherein R2 and R3 are both H.
- 31. A kit for forming an amide bond which comprises one or more phosphine-borane complexes of claim 1.
- 32. A kit for forming an amide bond which comprises one or more phoshine-borane complexes of claim 9.
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application takes priority under 35 U.S.C. 119(e) from U.S. provisional application serial no. 60/387,171, filed Jun. 7, 2003 which is incorporated by reference herein to the extent that it is not inconsistent with the disclosure herein.
STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT
[0002] This invention was made with U.S. Government support under National Institutes of Health Grant No. GM44783. The Government has certain rights in this invention.
Provisional Applications (1)
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Number |
Date |
Country |
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60387171 |
Jun 2002 |
US |