Described herein are synthetic glycan conjugates comprising a carrier and a glycan moiety derived from Neisseria meningitidis, wherein the glycan moiety is covalently linked to the carrier through a linker. Also provided herein are a mixture of the glycan conjugates thereof, immmunogenic composition
Described herein are synthetic glycan conjugates comprising a carrier and a glycan moiety derived from Neisseria meningitidis, wherein the glycan moiety is covalently linked to the carrier through a linker. Also provided herein are a mixture of the glycan conjugates thereof, immmunogenic compositions thereof, and kits thereof. The invention further provides methods of using the synthetic glycan conjugates and immunogenic compositions thereof to treat and/or reduce the risk of infectious diseases such as bacterial infections.
대표청구항▼
1. A homogeneous population of a glycan conjugate or a pharmaceutically acceptable salt thereof, comprising a carrier and a glycan wherein the glycan conjugate is of Formula (I-a) wherein each instance of R1, R2, R3, R4, R5, R6, and R7 is independently hydrogen, optionally substituted C1-6 alkyl, o
1. A homogeneous population of a glycan conjugate or a pharmaceutically acceptable salt thereof, comprising a carrier and a glycan wherein the glycan conjugate is of Formula (I-a) wherein each instance of R1, R2, R3, R4, R5, R6, and R7 is independently hydrogen, optionally substituted C1-6 alkyl, or an oxygen protecting group; or optionally R1 and R2 are taken with the intervening atoms to form a heterocyclic ring; or optionally R2 and R3 are taken with the intervening atoms to form a heterocyclic ring; or optionally R5 and R6 are taken with the intervening atoms to form a heterocyclic ring; or optionally R6 and R7 are taken with the intervening atoms to form a heterocyclic ring; or RN1 and RO1 are taken together with the intervening atoms to form a heterocyclic ring;each instance of RN1, RN2, and RBN is independently hydrogen, optionally substituted C1-6 alkyl, optionally substituted acyl, or a nitrogen protecting group;each instance of RO1 is independently hydrogen, optionally substituted C1-6 alkyl, or an oxygen protecting group;each instance of L is independently a bond, —C(═O)—, —C(═O)NRLa—, —C(═O)S—, —C(═O)O—, —C(═S)NRLa—, trans-CRLb═CRLb—, cis-CRLb═CRLb—, —C═C—, —C(RLb)2O—, —C(RLb)2NRLa—, —C(RLb)2S—, —S(═O)2O—, —S(═O)2NRLa—, or an optionally substituted C1-30 hydrocarbon chain, optionally wherein one or more carbon units of the hydrocarbon chain is replaced with —O—, —S—, —NRLa—, —C(═O)—, —NRLaC(═O)—, —NRLaC(═O)O—, —C(═O)NRLa—, —OC(═O)NRLa—, —SC(═O)—, —C(═O)S—, —OC(═O)—, —C(═O)O—, —NRLaC(═S)—, —C(═S)NRLa—, trans-CRLb═CRLb—, cis-CRLb═CRLb—, —C≡C—, —S(═O)2O—, —OS(═O)2—, —S(═O)2NRLa—, or —NRLaS(═O)2—, wherein each instance of RLa is hydrogen, optionally substituted C1-15 alkyl, or a nitrogen protecting group, or RLa is joined with the adjacent carbon atom to form an optionally substituted heterocyclic ring, and wherein each occurrence of RLb is independently selected from the group consisting of hydrogen, halogen, optionally substituted C1-15 alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl, or RLb is joined with the adjacent carbon or nitrogen or oxygen atom to form an optionally substituted carbocyclic or heterocyclic ring, or two RLb groups are joined to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring;each instance of L1 is independently a bond, —O—, —S—, —NRL1a—, —C(═O)—, —NRL1aC(═O)—, —NRL1aC(═O)O—, —C(═O)NRL1a—, —OC(═O)NRL1a—, —SC(═O)—, —C(═O)S—, —OC(═O)—, —C(═O)O—, —NRL1aC(═S)—, —C(═S)NRL1a—, trans-CRL1b═CRL1b—, cis-CRL1b═CRL1b—, —C≡C—, —OC(RL1b)2—, —C(RL1b)2O—, —NRL1aC(RL1b)2—, —C(RL1b)2NRL1a—, —SC(RL1b)2—, —C(RL1b)2S—, —S(═O)2O—, —OS(═O)2—, —S(═O)2NRL1a—, —NRL1aS(═O)2—, or an optionally substituted C1-20 hydrocarbon chain, optionally wherein one or more carbon units of the hydrocarbon chain is replaced with —O—, —S—, —NRL1a—, —C(═O)—, —NRL1aC(═O)—, —NRL1aC(═O)O—, —C(═O)NRL1a—, —OC(═O)NRL1a—, —SC(═O)—, —C(═O)S—, —OC(═O)—, —C(═O)O—, —NRL1aC(═S)—, —C(═S)NRL1a—, trans-CRL1b═CRL1b—, cis-CRL1b═CRL1b—, —C≡C≠, —S(═O)2O—, —OS(═O)2—, —S(═O)2NRL1a—, or —NRL1aS(═O)2—, wherein each instance of RL1a is hydrogen, optionally substituted C1-6 alkyl, or a nitrogen protecting group, or RL1a is joined with the adjacent carbon atom to form an optionally substituted heterocyclic ring, and wherein each occurrence of RL1b is independently selected from the group consisting of hydrogen, halogen, optionally substituted C1-10 alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl, or RL1b is joined with the adjacent carbon or nitrogen or oxygen atom to form an optionally substituted carbocyclic or heterocyclic ring, or two RL1b groups are joined to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring;each instance of L2 is independently a moiety derived from a crosslinking reagent capable of crosslinking the carrier and L1-H;each instance of L3C is independently a crosslinking reagent capable of crosslinking the carrier and L1-H;each instance of RCN is independently hydrogen, optionally substituted C1-6 alkyl, optionally substituted acyl, or a nitrogen protecting group;w is an integer of 1 to 100, inclusive; andy is 0 or an integer of 1 to 100, inclusive;p is an integer of 1 to 10, inclusive; andn is an integer of 1 to 100, inclusive. 2. The glycan conjugate of claim 1, wherein w is an integer of 1 to 10, inclusive. 3. The glycan conjugate of claim 1, wherein y is 0 or an integer of 1 to 10, inclusive. 4. The glycan conjugate of any one of claims 1-3, wherein p is 5. 5. The glycan conjugate of any one of claims 1-3, wherein R1, R2, R4, R5, R6, and R7 are hydrogen. 6. The glycan conjugate of any one of claims 1-3, wherein RN1 is acetyl. 7. The glycan conjugate of any one of claims 1-3, wherein RN2 is hydrogen. 8. The glycan conjugate of any one of claim 1-3, wherein RBN is hydrogen. 9. The glycan conjugate of any one of claims 1-3, wherein RCN is hydrogen. 10. The glycan conjugate of any one of claims 1-3, wherein the carrier is a protein, a lipolized protein, a virus, a peptide comprising a T cell epitope, or a dendrimer of glycopeptides. 11. The glycan conjugate of claim 10, wherein the carrier is a toxin protein selected from the group consisting of diphtheria toxin cross-reacting material 197 (DT-CRM197), diphtheria toxoid, tetanus toxoid, and outer-membrane protein (OMP). 12. The glycan conjugate of claim 11, wherein the toxin protein is DT-CRM197. 13. A glycan conjugate of the formula: wherein n is an integer of 1 to 100, inclusive;w is an integer of 1 to 100, inclusive; andy is 0 or an integer of 1 to 100, inclusive. 14. A glycan conjugate mixture comprising at least two of the glycan conjugates of claim 13. 15. The glycan conjugate mixture of claim 14, wherein the average value of w in the mixture is from about 1.0 to about 100.0. 16. The glycan conjugate mixture of claim 15, wherein the average value of w in the mixture is from about 1.0 to 10.0. 17. The glycan conjugate mixture of claim 16, wherein the average value of w is about 5.7, 4.9, 2.9, 2.8, or 3.1. 18. An immunogenic composition, comprising (i) a glycan conjugate of any one of claim 1 or 13; and(ii) a pharmaceutically acceptable excipient. 19. The immunogenic composition of claim 18, further comprising an adjuvant. 20. The immunogenic composition of claim 19, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 21. A kit comprising a glycan conjugate according to any one of claims 1-3 or an immunogenic composition comprising a glycan conjugate according to any one of claim 1 or 13 with a pharmaceutically acceptable excipient, and instructions for use thereof. 22. A method of preparing a glycan conjugate of claim 1, comprising coupling a compound of Formula (C-1) or a salt thereof, with a compound of the Formula (C-2) wherein L2C is a crosslinking reagent capable of crosslinking an amino group and L1-H. 23. The method of claim 22, wherein L2C is a crosslinking reagent capable of crosslinking an amine group and —SH. 24. The method of claim 22, wherein L2C is one of the following formulae: or a salt thereof, wherein each instance of RP1 and RP2 are each independently hydrogen, halogen, or optionally substituted C1-6 alkyl;each instance of R2Ca is a leaving group selected from selected from —Br, —Cl, —I, —OS(═O)2R2CO, or —OS(═O)R2CO, wherein R2CO is selected from the group consisting of optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl,optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl; andeach of t and i is independently an integer of 1 to 8, inclusive. 25. The method of any one of claim 22-24, wherein the molar ratio of the compound of Formula (C-1) to the compound of Formula (C-2) is from about 1 to about 100. 26. The method of any one of claims 22-25, wherein the coupling is carried out in the presence of phosphate buffered saline (PBS). 27. The method of any one of claims 22-26, further comprising glycosylating a compound of Formula (C-3) with a compound of Formula (C-4) to give a compound of Formula (C-5) wherein v is an integer of 1 to 99, inclusive;u is 0, 1, 2, 3, 4, or 5;each occurrence of RE is independently halogen, —CN, —NO2, —N3, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted phenyl, optionally substituted heterocyclyl, optionally substituted heteroaryl, —ORCE, —N(RCE)2, —SRE, —C(═O)RCE, —C(═O)ORCE, or —C(═O)N(RCE)2, wherein each RCE is independently selected from the group consisting of hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl; or an oxygen protecting group when attached to an oxygen, or a nitrogen protecting group when attached to nitrogen, or a sulfur protecting group when attached to sulfur; andRN3 is independently hydrogen, optionally substituted alkyl, or a nitrogen protecting group. 28. The method of claim 27, further comprising reacting the compound of Formula (C-5) in the presence of a base to give a compound of Formula (C-6) 29. The method of claim 28, wherein the base is NaOCH3. 30. The method of claim 28, further comprising reacting the compound of Formula (C-6) with a reducing agent to give a compound of Formula (C-7) 31. The method of any one of claim 30, further comprising (a) activating a compound of Formula (C-7) to give a compound of Formula (C-1); and (b) activating a carrier to give a compound of Formula (C-2). 32. The kit of claim 21, wherein the immunogenic composition further comprises an adjuvant. 33. The kit of claim 32, wherein the adjuvant is selected from C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21.
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