Claims
- 1. A compound having the structure:
- 2. The compound of claim 1 wherein L1 is —O—(CH2)n— and the compound has the structure:
- 3. The compound of claim 1, wherein L1 comprises a glycoside moiety.
- 4. The compound of claim 3, wherein the glycoside moiety is a monosaccharide.
- 5. The glycopeptide of claim 4, wherein the monosaccharide is a moiety having the structure:
- 6. The compound of claim 1, wherein R is —CH2CH(CO2R′)(NHR″)— and the compound has the structure:
- 7. The compound of claim 6, wherein L1 is —O(CH2)n— and the compound has the structure:
- 8. The compound of claim 6 or 7, wherein R′ and R″ are each protecting groups independently selected from the group consisting of Fmoc, acetyl, Benzyl, Boc, t-butyl, Cbz and TSE.
- 9. The compound of claim 7, wherein n is 3.
- 10. The compound of claim 1, wherein R is an immunogenic carrier.
- 11. The compound of claim 10 wherein the immunogenic carrier is a protein, peptide or lipid.
- 12. The compound of claim 11 wherein the carrier is KLH, polylysine or BSA.
- 13. The compound of claim 11 wherein the lipid has the structure:
- 14. The compound of claim 13, wherein m′, n′ and p′ are each 14 and the lipid is tripalmitoyl-S-glycerylcysteinylserine.
- 15. A multi-antigenic glycopeptide comprising a peptidic backbone made up of two or more amino acids, wherein one or more of said amino acids is/are independently substituted with a glycosidic moiety having the structure:
- 16. The glycopeptide of claim 15 wherein at least one occurrence of L1 is —O—(CH2)n—.
- 17. The glycopeptide of claim 16, wherein n is 3.
- 18. The glycopeptide of claim 15, wherein at least one occurrence of L1 comprises α-glycoside moiety.
- 19. The glycopeptide of claim 18, wherein the glycoside moiety is a monosaccharide.
- 20. The glycopeptide of claim 19, wherein the monosaccharide is a moiety having the structure:
- 21. The glycopeptide of claim 15, wherein said glycopeptide is a construct having the structure:
- 22. The glycopeptide of claim 21 wherein the linker is —O—, —NRG—, —NRG(aliphatic)NRJ—, —NRG(heteroaliphatic)NRJ—, -(aliphatic)NRJ—, -(heteroaliphatic)NRJ—, —O(aliphatic)NRJ—, —O(heteroaliphatic)NRJ—, —NRG(aliphatic)NRJ(C═O)(CRHRI)kS—, —NRG(heteroaliphatic)NRJ(C═O)(CRHRI)kS—, -(aliphatic)NRJ(C═O)(CRHRI)kS—, -(heteroaliphatic)NRJ(C═O)(CRHRI)kS—, —O(aliphatic)NRJ(C═O)(CRHRI)kS—, —O(heteroaliphatic)NRJ(C═O)(CRHRI)kS—, an oligoester fragment comprising from 2 to about 20 hydroxy acyl residues, a peptidic fragment comprising from 2 to about 20 amino acyl residues, or a linear or branched chain alkyl or aryl carboxylic ester, wherein each occurrence of k is independently 1-5; wherein each occurrence of RG, RH, RI or RJ is independently hydrogen, a linear or branched, substituted or unsubstituted, cyclic or acyclic moiety, or a substituted or unsubstituted aryl moiety, and wherein each aliphatic or heteroaliphatic moiety is independently substituted or unsubstituted, linear or branched, cyclic or acyclic.
- 23. The glycopeptide of claim 21, wherein the linker is —O—, —NRG(CRHRI)kNRJ—, —NRG(CRHRI)kNRJ(C═O)(CRHRI)kS—, —NRG—, —(CRHRJ)kNRI—, —O(CRHRI)kNRJ, an oligoester fragment comprising from 2 to about 20 hydroxy acyl residues, a peptidic fragment comprising from 2 to about 20 amino acyl residues, or a linear or branched chain alkyl or aryl carboxylic ester, wherein each occurrence of k is independently 1-5, wherein each occurrence of RG, RH, RI or RJ is independently hydrogen, a linear or branched, substituted or unsubstituted, cyclic or acyclic moiety, or a substituted or unsubstituted aryl moiety.
- 24. The glycopeptide of claim 21, wherein q is 1 and the crosslinker is a fragment having the structure:
- 25. The glycopeptide of claim 21 wherein R is hydrogen and q is 0.
- 26. The glycopeptide of claim 21 wherein R is an immunogenic carrier.
- 27. The compound of claim 26 wherein the immunogenic carrier is a protein, peptide or lipid.
- 28. The compound of claim 27 wherein the carrier is KLH, polylysine or BSA.
- 29. The compound of claim 27 wherein q is 0 and the lipid has the structure:
- 30. The compound of claim 29, wherein m′, n′ and p′ are each 14 and the lipid is tripalmitoyl-S-glycerylcysteinylserine.
- 31. The glycopeptide of claim 21 wherein at least one occurrence of L1 is —O—(CH2)n—, wherein ni is an integer from 0-9.
- 32. The glycopeptide of claim 31, wherein n is 3.
- 33. The glycopeptide of claim 21, wherein at least one occurrence of L1 comprises a glycoside moiety.
- 34. The glycopeptide of claim 33, wherein the glycoside moiety is a monosaccharide.
- 35. The glycopeptide of claim 34, wherein the monosaccharide is a moiety having the structure:
- 36. The glycopeptide of claim 21, wherein each occurrence of A which is not a carbohydrate domain having the structure:
- 37. The glycopeptide of claim 21, wherein m is 2, at least one occurrence of L1 is —O(CH2)n—, wherein n is an integer from 0-9; and each occurrence of A is independently a carbohydrate domain having the structure:
- 38. The glycopeptide of claim 21, wherein m is 2, at least one occurrence of L1 comprises a glycoside moiety, and each occurrence of A is independently a carbohydrate domain having the structure:
- 39. The glycopeptide of claim 38, wherein the glycoside is a monosaccharide.
- 40. The glycopeptide of claim 39, wherein the monosaccharide is a moiety having the structure:
- 41. The glycopeptide of claim 21 wherein m is 2, each occurrence of L1 is independently —O(CH2)n—, the glycopeptide has three occurrences of A comprising Gb3, and the glycopeptide has the structure:
- 42. The glycopeptide of claim 21 wherein m is 2, each occurrence of L1 independently comprises a monosaccharide, the glycopeptide has three occurrences of A comprising Gb3, and the glycopeptide has the structure:
- 43. The glycopeptide of claim 42, wherein each occurrence of n is 0.
- 44. The glycopeptide of claim 41, wherein each occurrence of n is 3.
- 45. The glycopeptide of claim 41 or 42, wherein q is 0.
- 46. The glycopeptide of claim 41 or 42, wherein R is KLH, Bovine Serum Albumin or polylysine.
- 47. The glycopeptide of claim 41 or 42, wherein the linker is a moiety having the structure —NH(CH2)tNHC(═O)(CH2)vS—; wherein t and v are each independently integers from 1-6.
- 48. The glycopeptide of claim 41 or 42, wherein each occurrence of Rx is hydrogen.
- 49. The glycopeptide of claim 42, wherein each occurrence of Ry is Ac.
- 50. The glycopeptide of claim 41 or 42, wherein q is 1 and the crosslinker is a moiety having the structure:
- 51. The glycopeptide of claim 42, wherein n and q are each 0, R is hydrogen and the linker is a moiety having the structure —NH(CH2)tNHC(═O)(CH2)vS— wherein t and v are each independently integers from 1-6.
- 52. The glycopeptide of claim 42, wherein n is 0, q is 1, R is KLH, the linker is a moiety having the structure —NH(CH2)tNHC(═O)(CH2)vS— wherein t and v are each independently integers from 1-6, and the crosslinker is a moiety having the structure:
- 53. The glycopeptide of claim 41, wherein q is 0, n is 3, R is hydrogen and the linker is a moiety having the structure —NH(CH2)tNHC(═O)(CH2)vS— wherein t and v are each independently integers from 1-6.
- 54. The glycopeptide of claim 41, wherein q is 1, n is 3, R is KLH, the linker is a moiety having the structure —NH(CH2)tNHC(═O)(CH2)vS— wherein t and v are each independently integers from 1-6, and the crosslinker is a moiety having the structure:
- 55. The glycopeptide of any one of claims 47, 51-54 wherein t is 3 and v is 1.
- 56. A glycopeptide having the structure:
- 57. A synthetic construct having the structure:
- 58. The construct of claim 57, wherein t′ is in the range of 20 to 600.
- 59. The construct of claim 57, wherein n is 4.
- 60. The glycopeptide of claim 21 or 56, wherein each occurrence of RA and RC is independently hydrogen or methyl.
- 61. A method for the synthesis of a glycoamino acid comprising steps of:
(a) providing a suitable alkenyl glycoside; (b) providing a suitably protected alkenylamino acid; (c) reacting said alkenyl glycoside with the alkenylamino acid suitable conditions in the presence of a suitable catalyst to generate a glycoenamide ester; and (d) subjecting the glycoenamide ester to suitable conditions to generate a glycoamino acid.
- 62. The method of claim 61 wherein:
the alkenyl glycoside of step (a) has the structure: 191wherein n is 0-8; A is a carbohydrate domain having the structure: 192wherein a, b, c, d, e, f, g, h, i, x, y and z are independently 0, 1, 2 or 3, with the proviso that the x, y and z bracketed structures represent furanose or pyranose moieties and the sum of b and c is 1 or 2, the sum of d and f is 1 or 2, and the sum of g and i is 1 or 2, and with the proviso that x, y and z are not simultaneously 0; wherein R0 is hydrogen, a linear or branched chain alkyl, acyl, arylalkyl or aryl group; wherein each occurrence of R1, R2, R3, R4, R5, R6, R7, R8 and R9 is independently hydrogen, OH, ORi, NHRi, NHCORi, F, CH2OH, CH2ORi, a substituted or unsubstituted linear or branched chain alkyl, (mono-, di- or tri)hydroxyalkyl, (mono-, di- or tri)acyloxyalkyl, arylalkyl or aryl group; wherein each occurrence of Ri is independently hydrogen, CHO, COORii, or a substituted or unsubstituted linear or branched chain alkyl, acyl, arylalkyl or aryl group or a saccharide moiety having the structure: 193wherein Y and Z are independently NH or O; wherein k, l, r, s, t, u, v and w are each independently 0, 1 or 2; with the proviso that the v and w bracketed structures represent furanose or pyranose moieties and the sum of l and k is 1 or 2, and the sum of s and u is 1 or 2, and with the proviso that v and w are not simultaneously 0; wherein R′0 is hydrogen, a linear or branched chain alkyl, acyl, arylalkyl or aryl group; wherein each occurrence of R10, R11, R12, R13, R14 and R15 is independently hydrogen, OH, ORiii, NHRiii, NHCORiii, F, CH2OH, CH2ORiii, or a substituted or unsubstituted linear or branched chain alkyl, (mono-, di- or tri)hydroxyalkyl, (mono-, di- or tri)acyloxyalkyl, arylalkyl or aryl group; wherein each occurrence of R16 is hydrogen, COOH, COORii, CONHRii, a substituted or unsubstituted linear or branched chain alkyl or aryl group; wherein each occurrence of Riii is hydrogen, CHO, COORiv, or a substituted or unsubstituted linear or branched chain alkyl, acyl, arylalkyl or aryl group; and wherein each occurrence of Rii and Riv are each independently H, or a substituted or unsubstituted linear or branched chain alkyl, arylalkyl or aryl group; the alkenylamino acid of step (b) is an alkenylglycine having the structure: 194wherein R′ and R″ are each independently hydrogen or a protecting group and q′ is an integer from 0-8; the glycoenamide ester generated in step (c) has the structure: 195wherein R′ and R″ are each independently hydrogen or a protecting group, and n and q′ are each independently an integer from 0-8; and the glycoamino acid generated in step (d) has the structure: 196wherein R′ and R″ are each independently hydrogen or a protecting group, and n and q′ are each independently an integer from 0-8.
- 63. The method of claim 61, wherein A is selected from the group consisting of Globo-H, fucosyl GM1, KH-1, glycophorin, STN, (2,3)ST, Ley, N3, Tn, STn, 2,6-STn, Gb3 and TF.
- 64. The method of claim 61, wherein A is a carbohydrate determinant having the structure:
- 65. The method of claim 61, wherein A is a carbohydrate determinant having the structure:
- 66. The method of claim 61, wherein A is a carbohydrate determinant having the structure:
- 67. The method of claim 61, wherein the catalyst of step (a) is selected from the group consisting of:
- 68. The method of claim 61, wherein the catalyst of step (a) has the structure:
- 69. The method of claim 61, wherein the step of reacting said glycoenamide ester under suitable conditions to generate a glycoamino acid comprises reacting said enamide ester under hydrogenation conditions and subsequent reaction under deprotection conditions to generate a glycoamino acid.
- 70. A pharmaceutical composition comprising:
a compound or glycopeptide of claim 1, 15, 21 or 56, and a pharmaceutically suitable carrier.
- 71. The pharmaceutical composition of claim 70, wherein the compound or glycopeptide is conjugated to an immunogenic carrier.
- 72. A pharmaceutical composition comprising:
a pharmaceutically acceptable carrier; an immunogenic carrier; and a multi-antigenic glycopeptide comprising a peptidic backbone made up of two or more amino acids, wherein one or more of said amino acids is/are independently substituted with a glycosidic moiety having the structure: 202wherein each occurrence of L1 is independently a substituted or unsubstituted aliphatic or heteroaliphatic moiety; each occurrence of A is independently a carbohydrate determinant having the structure: 203wherein a, b, c, d, e, f, g, h, i, x, y and z are independently 0, 1, 2 or 3, with the proviso that the x, y and z bracketed structures represent furanose or pyranose moieties and the sum of b and c is 1 or 2, the sum of d and f is 1 or 2, and the sum of g and i is 1 or 2, and with the proviso that x, y and z are not simultaneously 0; wherein R0 is hydrogen, a linear or branched chain alkyl, acyl, arylalkyl or aryl group; wherein each occurrence of R1, R2, R3, R4, R5, R6 , R7, R8 and R9 is independently hydrogen, OH, ORi, NHRi, NHCORi, F, CH2OH, CH2ORi, a substituted or unsubstituted linear or branched chain alkyl, (mono-, di- or tri)hydroxyalkyl, (mono-, di- or tri)acyloxyalkyl, arylalkyl or aryl group; wherein each occurrence of Ri is independently hydrogen, CHO, COORii, or a substituted or unsubstituted linear or branched chain alkyl, acyl, arylalkyl or aryl group or a saccharide moiety having the structure: 204wherein Y and Z are independently NH or O; wherein k, l, r, s, t, u, v and w are each independently 0, 1 or 2; with the proviso that the v and w bracketed structures represent furanose or pyranose moieties and the sum of l and k is 1 or 2, and the sum of s and u is 1 or 2, and with the proviso that v and w are not simultaneously 0; wherein R′0 is hydrogen, a linear or branched chain alkyl, acyl, arylalkyl or aryl group; wherein each occurrence of R10, R11, R12, R13, R14 and R15 is independently hydrogen, OH, ORiii, NHRiii, NHCORiii, F, CH2OH, CH2ORiii, or a substituted or unsubstituted linear or branched chain alkyl, (mono-, di- or tri)hydroxyalkyl, (mono-, di- or tri)acyloxyalkyl, arylalkyl or aryl group; wherein each occurrence of R16 is hydrogen, COOH, COORii, CONHRii, a substituted or unsubstituted linear or branched chain alkyl or aryl group; wherein each occurrence of Riii is hydrogen, CHO, COORiv, or a substituted or unsubstituted linear or branched chain alkyl, acyl, arylalkyl or aryl group; and wherein each occurrence of Rii and Riv are each independently H, or a substituted or unsubstituted linear or branched chain alkyl, arylalkyl or aryl group; whereby the glycopeptide has not been conjugated to the immunogenic carrier.
- 73. The pharmaceutical composition of claim 72, wherein each occurrence of A is independently Globo-H, fucosyl GM1, KH-1, glycophorin, STN, Ley, N3, Tn, 2,6-STn, (2,3)ST, Gb3 or TF.
- 74. The pharmaceutical composition of claim 71 or 72, wherein the immunogenic carrier is bovine serum albumin, polylysine or keyhole limpet hemocyanin.
- 75. The pharmaceutical composition of claim 71 or 72, wherein q is 0 and the immunogenic carrier is a lipid having the structure:
- 76. The pharmaceutical composition of claim 75, wherein m′, n′ and p′ are each 14 and the lipid is tripalmitoyl-S-glycerylcysteinylserine.
- 77. The pharmaceutical composition of claim 71 or 72, further comprising one or more immunological adjuvants.
- 78. The pharmaceutical composition of claim 77, wherein at least one of said one or more immunological adjuvants is a saponin adjuvant.
- 79. The pharmaceutical composition of claim 78, wherein the saponin adjuvant is GPI-0100.
- 80. The pharmaceutical composition of claim 77, wherein at least one of said one or more immunological adjuvants is bacteria or liposomes.
- 81. The pharmaceutical composition of claim 80, wherein the immunological adjuvant is Salmonella minnesota cells, bacille Calmette-Guerin or QS21.
- 82. A method of treating cancer in a subject suffering therefrom comprising:
administering to a subject a therapeutically effective amount of a compound or glycopeptide of claim 1, 15, 21 or 56, and a pharmaceutically suitable carrier.
- 83. The method of claim 82, wherein the compound or glycopeptide is conjugated to an immunogenic carrier.
- 84. The method of claim 82, wherein the compound or glycopeptide has not been conjugated to a carrier, and the method further comprises administering an immunogenic carrier.
- 85. The method of claim 82, wherein said method comprises preventing the recurrence of cancer in a subject.
- 86. The method of claim 82 or 85, wherein the cancer is a solid tumor.
- 87. The method of claim 82 or 85, wherein the subject is in clinical remission, or where the subject has been treated by surgery, has limited unresected disease.
- 88. A method of inducing antibodies in a subject, wherein the antibodies are capable of specifically binding with tumor cells, which comprises administering to the subject an amount of a compound or construct of claim 1, 15, 21 or 56 effective to induce the antibodies.
- 89. The method of claim 88, wherein the glycopeptide is conjugated to an immunogenic carrier.
- 90. A method of inducing antibodies in a subject, wherein the antibodies are capable of specifically binding with tumor cells, which comprises administering to the subject:
an amount of a multi-antigenic glycopeptide comprising a peptidic backbone made up of two or more amino acids, wherein one or more of said amino acids is/are independently substituted with a glycosidic moiety having the structure: 206wherein each occurrence of L1 is independently a substituted or unsubstituted aliphatic or heteroaliphatic moiety; each occurrence of A is independently a carbohydrate determinant having the structure: 207wherein a, b, c, d, e, f, g, h, i, x, y and z are independently 0, 1, 2 or 3, with the proviso that the x, y and z bracketed structures represent furanose or pyranose moieties and the sum of b and c is 1 or 2, the sum of d and f is 1 or 2, and the sum of g and i is 1 or 2, and with the proviso that x, y and z are not simultaneously 0; wherein R0 is hydrogen, a linear or branched chain alkyl, acyl, arylalkyl or aryl group; wherein each occurrence of R1, R2, R3, R4, R5, R6 , R7, R8 and R9 is independently hydrogen, OH, ORi, NHRi, NHCORi, F, CH2OH, CH2ORi, a substituted or unsubstituted linear or branched chain alkyl, (mono-, di- or tri)hydroxyalkyl, (mono-, di- or tri)acyloxyalkyl, arylalkyl or aryl group; wherein each occurrence of Ri is independently hydrogen, CHO, COORii, or a substituted or unsubstituted linear or branched chain alkyl, acyl, arylalkyl or aryl group or a saccharide moiety having the structure: 208wherein Y and Z are independently NH or O; wherein k, l, r, s, t, u, v and w are each independently 0, 1 or 2; with the proviso that the v and w bracketed structures represent furanose or pyranose moieties and the sum of l and k is 1 or 2, and the sum of s and u is 1 or 2, and with the proviso that v and w are not simultaneously 0; wherein R′0 is hydrogen, a linear or branched chain alkyl, acyl, arylalkyl or aryl group; wherein each occurrence of R10, R11, R12, R13, R14 and R15 is independently hydrogen, OH, ORiii, NHRiii, NHCORiii, F, CH2OH, CH2ORiii, or a substituted or unsubstituted linear or branched chain alkyl, (mono-, di- or tri)hydroxyalkyl, (mono-, di- or tri)acyloxyalkyl, arylalkyl or aryl group; wherein each occurrence of R16 is hydrogen, COOH, COORii, CONHRii, a substituted or unsubstituted linear or branched chain alkyl or aryl group; wherein each occurrence of Riii is hydrogen, CHO, COORiv, or a substituted or unsubstituted linear or branched chain alkyl, acyl, arylalkyl or aryl group; and wherein each occurrence of Rii and Riv are each independently H, or a substituted or unsubstituted linear or branched chain alkyl, arylalkyl or aryl group; whereby the glycopeptide has not been conjugated to an immunogenic carrier; and wherein the amount of glycopeptide is effective to induce the antibodies.
- 91. The method of claim 90, wherein the method further comprises administering an immunogenic carrier.
- 92. A method of inducing antibodies in a subject, wherein the antibodies are capable of specifically binding with tumor cells, which comprises administering to the subject an amount of a multi-antigenic glycopeptide effective to induce the antibodies, wherein the glycopeptide has the structure:
- 93. The method of any one of claims 90-92, wherein at least one occurrence of L1 is —O—(CH2)n—, wherein n is an integer from 0-9.
- 94. The method of claim 93, wherein n is 3.
- 95. The method of any one of claims 90-92, wherein at least one occurrence of L1 comprises a glycoside moiety.
- 96. The method of claim 95, wherein the glycoside moiety is a monosaccharide.
- 97. The method of claim 96, wherein the monosaccharide is a moiety having the structure:
- 98. The method of claim 90 or 92, wherein in the glycopeptide, each occurrence of A is independently a carbohydrate domain selected from the group consisting of Globo-H, fucosyl GM1, KH-1, glycophorin, STN, Ley, N3, Tn, 2,6-STn, (2,3)ST, or TF, a carbohydrate domain having the structure:
- 99. The method of claim 90 or 92, wherein the glycopeptide comprises at least two different carbohydrate antigens, and the antibodies induced recognize said carbohydrate antigens present on the peptidic backbone.
- 100. The method of claim 99, wherein the carbohydrate antigens present on the peptidic backbone independently comprise a carbohydrate domain, or truncated or elongated version thereof, that is present on tumor cells.
- 101. The method of claim 90 or 92, wherein the glycopeptide has three occurrences of A comprising Tn, Globo-H and Ley and the antibodies induced are those that recognize Tn, Globo-H and/or Ley antigens.
- 102. The method of claim 101, wherein the glycopeptide has the structure:
- 103. The method of claim 90 or 92, wherein the glycopeptide has three occurrences of A comprising Tn, TF and Ley and the antibodies induced are those that recognize Tn, TF and/or Ley antigens.
- 104. The method of claim 103, wherein the glycopeptide has the structure:
- 105. The method of claim 90 or 92, wherein the glycopeptide has five occurrences of A comprising Globo-H, Ley, STn, TF and Tn, and the antibodies induced are those that recognize Globo-H, Ley, STn, TF and/or Tn antigens.
- 106. The method of claim 105, wherein the glycopeptide has the structure:
- 107. The method of claim 82, 85, 88, 90 or 92, further comprising co-administering one or more immunological adjuvants.
- 108. The method of claim 107, wherein at least one of said one or more immunological adjuvants is a saponin adjuvant.
- 109. The method of claim 108, wherein said saponin adjuvant is GPI-0100.
- 110. The method of claim 107, wherein at least one of said one or more immunological adjuvants is bacteria or liposomes.
- 111. The method of claim 110, wherein the immunological adjuvant is Salmonella minnesota cells, bacille Calmette-Guerin or QS21.
- 112. The method of claim 110, wherein the immunological adjuvant is Salmonella minnesota cells, bacille Calmette-Guerin or QS21.
- 113. The method of claim 83, 84, 89, 91 or 92, wherein the immunogenic carrier is a protein, peptide or lipid.
- 114. The method of claim 113, wherein the carrier is KLH, BSA or polylysine.
- 115. The method of claim 113, the immunogenic carrier is a lipid having the structure:
- 116. The method of claim 115, wherein m′, n′ and p′ are each 14 and the lipid is tripalmitoyl-S-glycerylcysteinylserine.
- 117. The method of claim 92, wherein each occurrence of RA and RC is independently hydrogen or methyl.
PRIORITY INFORMATION
[0001] This application is a continuation-in-part of co-pending patent application Ser. No. 09/641,742 filed Aug. 18, 2000, which claims priority under § 119(e) of the United States Code to provisional application 60/150,088, filed Aug. 20, 1999, entitled “Synthesis and Bioconjugation of the n-Pentenyl Glycoside of the Tumor-Associated Antigen Fucosyl GM1”, each of which is hereby incorporated by reference in its entirety.
GOVERNMENT SUPPORT
[0002] The present invention was supported by the National Institutes of Health Grant Numbers: AI16943 and CA28824. Therefore, the government has certain rights in the present invention.
Provisional Applications (1)
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Number |
Date |
Country |
|
60150088 |
Aug 1999 |
US |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
09641742 |
Aug 2000 |
US |
Child |
10209618 |
Jul 2002 |
US |