US2003232452A1PendingUtilityA1
Linkers for synthesis of oligosaccharides on solid supports
Priority: Mar 5, 1999Filed: Jun 5, 2003Published: Dec 18, 2003
Est. expiryMar 5, 2019(expired)· nominal 20-yr term from priority
C40B 80/00C40B 50/18C07H 1/00C07B 2200/11C07H 3/06C07H 15/18C40B 40/12
51
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Claims
Abstract
In certain embodiments, the present invention relates to versatile linkers for tethering a molecule to a solid support, e.g., for tethering a monomer, oligomer or polymer to a solid support, which are stable to a wide range of reaction conditions, but can be cleaved under well-defined conditions, thereby liberating said molecule from the solid support. In preferred embodiments, the linkers of the present invention are used to tether to the solid support unprotected, partially-protected or fully-protected monosaccharides or oligosaccharides, or unprotected, partially-protected or fully-protected glycoconjugates. In other embodiments, the linkers of the present invention may be used to tether to solid supports building blocks useful in the assembly of libraries of other types of small molecules. In certain embodiments, the present invention relates to a molecule or plurality of molecules tethered to the solid support via a linker or linkers of the present invention. In certain embodiments, the present invention relates to processes for synthesizing molecules, e.g., monomers, oligomers or polymers, on a solid support, wherein a starting material in the synthesis of said molecule, intermediates in the synthesis of said molecule, and said molecule itself are tethered to the solid support during the process via one of the linkers of the present invention. In certain processes of the present invention, the molecule is liberated from the solid support by cleavage of the linker of the present invention.
Claims
exact text as granted — not AI-modifiedWe claim:
1 . A compound represented by general structure 9:
wherein
X independently for each occurrence represents O, S, Se, NR, PR or AsR;
Z independently for each occurrence represents CR, SiR, N, P or As;
R independently for each occurrence represents hydrogen, alkyl, aryl or heteroaryl;
R′ represents hydrogen or a solid support;
R″ represents hydrogen, a mono-, oligo- or polysaccharide, a glycoconjugate, or a small molecule;
n is 3; and
m is an integer greater than or equal to 2.
2 . The compound of claim 1 , wherein X independently for each occurrence represents O, S, or NR.
3 . The compound of claim 1 , wherein X independently for each occurrence represents O.
4 . The compound of claim 1 , wherein Z independently for each occurrence represents CR or N.
5 . The compound of claim 1 , wherein Z independently for each occurrence represents CR.
6 . The compound of claim 1 , wherein X independently for each occurrence represents O, S, or NR; and Z independently for each occurrence represents CR or N.
7 . The compound of claim 1 , wherein X independently for each occurrence represents O; and Z independently for each occurrence represents CR or N.
8 . The compound of claim 1 , wherein X independently for each occurrence represents O; and Z independently for each occurrence represents CR.
9 . The compound of claim 1 , wherein R independently for each occurrence represents hydrogen or alkyl.
10 . The compound of claim 1 , wherein X independently for each occurrence represents O, S, or NR; and R independently for each occurrence represents hydrogen or alkyl.
11 . The compound of claim 1 , wherein X independently for each occurrence represents O; and R independently for each occurrence represents hydrogen or alkyl.
12 . The compound of claim 1 , wherein Z independently for each occurrence represents CR or N; and R independently for each occurrence represents hydrogen or alkyl.
13 . The compound of claim 1 , wherein Z independently for each occurrence represents CR; and R independently for each occurrence represents hydrogen or alkyl.
14 . The compound of claim 1 , wherein X independently for each occurrence represents O, S, or NR; Z independently for each occurrence represents CR or N; and R independently for each occurrence represents hydrogen or alkyl.
15 . The compound of claim 1 , wherein X independently for each occurrence represents O; Z independently for each occurrence represents CR or N; and R independently for each occurrence represents hydrogen or alkyl.
16 . The compound of claim 1 , wherein X independently for each occurrence represents O; Z independently for each occurrence represents CR; and R independently for each occurrence represents hydrogen or alkyl.
17 . The compound of claim 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , or 16 , wherein R′ represents a solid support.
18 . The compound of claim 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , or 16 , wherein R′ represents H.
19 . The compound of claim 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , or 16 , wherein R″ represents H.
20 . The compound of claim 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , or 16 , wherein R″ represents a monosaccharide or oligosaccharide.
21 . The compound of claim 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , or 16 , wherein R″ represents a monosaccharide, wherein the anomeric carbon of said monosaccharide is bonded to X.
22 . The compound of claim 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , or 16 , wherein R″ represents an oligosaccharide, wherein an anomeric carbon of said oligosaccharide is bonded to X.
23 . The compound of claim 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , or 16 , wherein R′ represents a solid support; and R″ represents H.
24 . The compound of claim 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , or 16 , wherein R′ represents a solid support; and R″ represents a monosaccharide or oligosaccharide.
25 . A compound represented by generalized structure 10:
wherein
X independently for each occurrence represents O, S, Se, NR, PR or AsR;
R independently for each occurrence represents hydrogen, alkyl, aryl or heteroaryl;
R′ represents hydrogen or a solid support;
R″ represents hydrogen, a mono-, oligo- or polysaccharide, a glycoconjugate, or a small molecule;
n is 3; and
m is an integer greater than or equal 2.
26 . The compound of claim 25 , wherein X independently for each occurrence represents O, S, or NR.
27 . The compound of claim 25 , wherein X independently for each occurrence represents O.
28 . The compound of claim 25 , wherein R independently for each occurrence represents hydrogen or alkyl.
29 . The compound of claim 25 , wherein X independently for each occurrence represents O, S, or NR; and R independently for each occurrence represents hydrogen or alkyl.
30 . The compound of claim 25 , wherein X independently for each occurrence represents O; and R independently for each occurrence represents hydrogen or alkyl.
31 . The compound of claim 25 , 26 , 27 , 28 , 29 or 30 , wherein R′ represents a solid support.
32 . The compound of claim 25 , 26 , 27 , 28 , 29 or 30 , wherein R′ represents H.
33 . The compound of claim 25 , 26 , 27 , 28 , 29 or 30 , wherein R″ represents H.
34 . The compound of claim 25 , 26 , 27 , 28 , 29 or 30 , wherein R″ represents a monosaccharide or oligosaccharide.
35 . The compound of claim 25 , 26 , 27 , 28 , 29 or 30 , wherein R″ represents a monosaccharide, wherein the anomeric carbon of said monosaccharide is bonded to X.
36 . The compound of claim 25 , 26 , 27 , 28 , 29 or 30 , wherein R″ represents an oligosaccharide, wherein an anomeric carbon of said oligosaccharide is bonded to X.
37 . The compound of claim 25 , 26 , 27 , 28 , 29 or 30 , wherein R″ represents a solid support; and R″ represents H.
38 . The compound of claim 25 , 26 , 27 , 28 , 29 or 30 , wherein R′ represents a solid support; and R″ represents a monosaccharide or oligosaccharide.
39 . A compound represented by generalized structure 11:
wherein
X independently for each occurrence represents O, S, Se, NR, PR or AsR;
R independently for each occurrence represents hydrogen, alkyl, aryl or heteroaryl;
R′ represents hydrogen or a solid support;
R″ represents hydrogen, a mono-, oligo- or polysaccharide, a glycoconjugate, or a small molecule;
n is 3; and
m is an integer greater than or equal 2.
40 . The compound of claim 39 , wherein X independently for each occurrence represents O, S, or NR.
41 . The compound of claim 39 , wherein X independently for each occurrence represents 0.
42 . The compound of claim 39 , wherein R independently for each occurrence represents hydrogen or alkyl.
43 . The compound of claim 39 , wherein X independently for each occurrence represents O, S, or NR; and R independently for each occurrence represents hydrogen or alkyl.
44 . The compound of claim 39 , wherein X independently for each occurrence represents O; and R independently for each occurrence represents hydrogen or alkyl.
45 . The compound of claim 39 , 40 , 41 , 42 , 43 or 44 , wherein R′ represents a solid support.
46 . The compound of claim 39 , 40 , 41 , 42 , 43 or 44 , wherein R″ represents H.
47 . The compound of claim 39 , 40 , 41 , 42 , 43 or 44 , wherein R″ represents H.
48 . The compound of claim 39 , 40 , 41 , 42 , 43 or 44 , wherein R″ represents a monosaccharide or oligosaccharide.
49 . The compound of claim 39 , 40 , 41 , 42 , 43 or 44 , wherein R″ represents a monosaccharide, wherein the anomeric carbon of said monosaccharide is bonded to X.
50 . The compound of claim 39 , 40 , 41 , 42 , 43 or 44 , wherein R″ represents an oligosaccharide, wherein an anomeric carbon of said oligosaccharide is bonded to X.
51 . The compound of claim 39 , 40 , 41 , 42 , 43 or 44 , wherein R′ represents a solid support; and R″ represents H.
52 . The compound of claim 39 , 40 , 41 , 42 , 43 or 44 , wherein R′ represents a solid support; and R″ represents a monosaccharide or oligosaccharide.
53 . A process of synthesis, comprising the step of:
reacting a linker of claim 1 , 25 or 39 , wherein R′ represents a solid support, with a compound to give a linker of claim 1 , 25 or 39 , wherein R′ represents a solid support, and R″ comprises said compound.
54 . The process of claim 53 , wherein said compound is a monosaccharide or oligosaccharide.
55 . The process of claim 53 or 54 , further comprising the step of:
cleaving said linker to give a product that is not tethered to a solid support.
56 . The process of claim 55 , wherein said product is an oligosaccharide.
57 . The process of claim 53 or 54 , further comprising the step of:
cleaving said linker to give a product that is not tethered to a solid support, wherein said product is an oligosaccharide comprising a glycosyl donor.
58 . The process of claim 53 or 54 , further comprising the step of:
cleaving said linker by ozonolysis, olefin metathesis, or oxidation to give a product that is not tethered to a solid support.
59 . The process of claim 58 , wherein said product is an oligosaccharide.
60 . The process of claim 58 , wherein said product is an oligosaccharide comprising a glycosyl donor.
61 . The process of claim 53 or 54 , further comprising the step of:
cleaving said linker by olefin metathesis to give a product that is not tethered to a solid support, wherein said product is an oligosaccharide comprising an n-pentenyl glycoside.Join the waitlist — get patent alerts
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