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US 12,152,053 B2Granted
Oligosaccharide analytical standards
AssigneeUniversity of Georgia Research Foundation, Inc.
InventorsGeert-Jan Boons, Anthony Robert Prudden, Lin Liu
Life of this patent
Estimating the term…
Abstract
Disclosed herein are oligosaccharides and intermediates useful for the production thereof. The compounds are useful as analytical standards and as intermediates for the preparation of more complex oligosaccharide and N-glycan products. The compounds may be prepared in high purity using the selective stop/go synthetic methods disclosed herein.
Claims16
A compound represented by the following structural formula:
- or a pharmaceutically acceptable salt thereof, wherein:
- R1 is OH or a residue represented by the following structural formula:
- wherein:
- n is 1 or 0;
- Rfa is H or a fucose residue represented by the following formula:
- and
- R2 is ORc, NR2nORc, or NR2aRc, wherein R2n is H or a C1-4 alkyl, and Rc is H, or a C1-8 alkyl;
- R4 is N3 or NR4aR4b, wherein R4a and R4b, each independently, is H or Z—X4, wherein Z is null, C═O, SO2, and X4 is C1-4alkyl or C1-4haloalkyl;
- R5 is N3 or NR5aR5b, wherein R5a and R5b, each independently, is H or Z—X5, wherein Z is null, C═O, SO2, and X4 is C1-4alkyl or C1-4haloalkyl
- R6 is hydrogen or a residue represented by the following formula:
- wherein R9 is N3 or NR9aR9b, wherein R9a and R9b, each independently, is H or Z—X9, wherein Z is null, C═O, SO2, and X9 is C1-4alkyl or C1-4haloalkyl;
- R7 is hydrogen or a residue having the formula:
- wherein:
- R10 is N3 or NR10aR10b, wherein R10a and R10b, each independently, is H or Z—X10, wherein Z is null, C═O, SO2, and X4 is C1-4alkyl or C1-4haloalkyl;
- and
- R12 is hydrogen or a residue represented by the formula:
- wherein:
- R13 is hydrogen or a residue represented by the formula:
- wherein R13b is H and R13a is OH;
- R14 is hydrogen or a residue having the formula:
- wherein R14b is H and R14a is OH;
- R8 is hydrogen or a residue represented by the following formula:
- wherein
- R11 is N3 or NR11aR11b, wherein R11a and R11b, each independently, is H or Z—X11, wherein Z is null, C═O, SO2, and X11 is C1-4alkyl or C1-4haloalkyl;
- R15 is hydrogen or a residue represented by the following formula:
- wherein:
- R17 is hydrogen or a residue represented by the following formula:
- wherein R17b is H and R17a is OH;
- R18 is hydrogen or a residue having the formula:
- wherein R18b is H and R18a is OH;
- and
- R16 is hydrogen or a residue represented by the following formula:
- wherein R19 is hydrogen or a residue represented by the following formula:
- wherein R19b is H, and R19a is OH;
- R20 is hydrogen or a residue having the formula:
- wherein R20b is H and R20a is OH.
33 more elements
Dependencies are inferred from the claim text.