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US 12,162,901 B2Granted
N-acetylated sialic acids and related sialosides
AssigneeThe Regents of the University of California
InventorsXi Chen, An Xiao, Anoopjit Kooner, Abhishek Santra, Ajit Varki, Hai Yu, Lee-Ping Wang, Wanqing Li
Life of this patent
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Abstract
The present invention provides N-acetyl derivatives of sialic acids, including N-acetyl derivatives of Neu5Ac and Neu5Gc. Methods for preparing related precursors and a variety of sialosides are also disclosed.
Claims8
A compound according to Formula IVa:
- wherein:
- R1 is —NHAc;
- R2, R3, and R4 are independently selected from the group consisting of —NHAc, —NH2, and —OH;
- wherein at least one of R2, R3, and R4 is —NHAc or —NH2;
- R5 is selected from the group consisting of —NHR5a, —OH, and —OAc;
- R5ª is selected from the group consisting of Ac, Gc, GcAc, GcN3, GcNH2, GcNAc, and hydrogen;
- Ac is —C(O)CH3;
- Gc is —C(O)CH2OH;
- GcAc is —C(O)CH2OC(O)CH3;
- GcN3 is —C(O)CH2N3;
- GcNH2 is —C(O)CH2NH2;
- GcNAc is —C(O)CH2NHC(O)CH3;
- and
- R6 is selected from the group consisting of a galactoside, an N-acetylgalactosaminide, a glucoside, an N-acetylglucosaminide, and a sialoside.
11 more elements
A compound according to Formula IVa:
- wherein:
- R1 is —NHAc;
- R2, R3, and R4 are independently selected from the group consisting of —NHAc, —NH2, and —OH;
- R5 is selected from the group consisting of —NHR5a, —OH, and —OAc;
- R5a is selected from the group consisting of Gc, GcAc, GcN3, GcNH2, GcNAc, and hydrogen;
- Ac is —C(O)CH3;
- Gc is —C(O)CH2OH;
- GcAc is —C(O)CH2OC(O)CH3;
- GcN3 is —C(O)CH2N3;
- GcNH2 is —C(O)CH2NH2;
- GcNAc is —C(O)CH2NHC(O)CH3;
- and
- R6 is selected from the group consisting of a galactoside, an N-acetylgalactosaminide, a glucoside, an N-acetylglucosaminide, and a sialoside.
10 more elements
A compound according to Formula IVa:
- wherein:
- R1 is —OH;
- R2, R3, and R4 are independently selected from the group consisting of —NHAc, —NH2, and —OH;
- R5 is selected from the group consisting of —NHR5a, —OH, and —OAc;
- R5a is selected from the group consisting of GcAc, GcN3, GcNH2, GcNAc, and hydrogen;
- GcAc is —C(O)CH2OC(O)CH3;
- GcN3 is —C(O)CH2N3;
- GcNH2 is —C(O)CH2NH2;
- GcNAc is —C(O)CH2NHC(O)CH3;
- and
- R6 is selected from the group consisting of a galactoside, an N-acetylgalactosaminide, a glucoside, an N-acetylglucosaminide, and a sialoside.
8 more elements
Dependencies are inferred from the claim text.