US3950322A
Expired / Lapsed
US
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Fluorogenic substrate glycosides
Assignee: Research Corp
•
Filing: 1973-08-27
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Granted: 1976-04-13
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Expires: 1993-08-27
Abstract
Abstract There are provided novel fluorogenic substrates comprising a ketoside formed between an N-acyl neuraminic acid and a highly fluorescent material containing a phenolic grouping. The presence of neuraminidase is detected by contacting the aforementioned fluorogenic substrate with a sample suspected of containing neuraminidase. Neuraminidase, if present, cleaves the ketosidic linkage, releasing the fluorescent material which is then detected by known methods. There is also provided a novel and efficient method of preparing such fluorogenic substrates utilizing cadmium carbonate as a catalyst.
Inventors
- 👤 John J. Thomas
- 👤 Edward C. Folger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 19:23
CPC Classifications
C; C07; C07H; C07H13/00; C07H13/02; C07H13/04; C07H17/00; C07H17/04; C07H17/06; C07H17/065; C07H17/075; C07H21/00; C12; C12Q; C12Q1/00; C12Q1/34; C12Q1/70; C12Q2334/00; C12Q2334/20; C12Q2334/22; C12Q2334/40; G; G01; G01N; G01N2333/00; G01N2333/90; G01N2333/914; G01N2333/924; Y; Y10; Y10S; Y10S435/00; Y10S435/808
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
25 words
2,0-Flu-(N acetyl-neuraminic acid) wherein Flu is an aryl moiety whose origin HO.Flu is selected from the group consisting of fluoroescein, methylfluoroscein, methylumbelliferone, umbelliferone and resorufine.
Claim 2
Dependent Claim
25 words
2,0-Flu-(N acetyl-neuraminic acid) wherein Flu is an aryl moiety whose origin HO.Flu is selected from the group consisting of fluoroescein, methylfluoroscein, methylumbelliferone, umbelliferone and resorufine.
Claim 3
Dependent Claim
8 words
2-0-4-methylumbelliferyl-N-acetyl-α-D-neuraminic acid being a compound of claim 1.
Claim 4
Dependent Claim
8 words
2-0-fluoresceinyl-N-acetyl-α-D-neuraminic acid being a compound of claim 1.
Claim 5
Dependent Claim
8 words
2-0-umbelliferyl-N-acetyl-α-D-neuraminic acid being a compound of claim 1.
Claim 6
Dependent Claim
8 words
2-0-methylfluoresceinyl-N-acetyl-α-D-neuraminic acid being a compound of claim 1.
Claim 7
Dependent Claim
8 words
2-0-resorufinyl-N-acetyl-α-D-neuraminic acid being a compound of claim 1.
Claim 8
Dependent Claim
65 words
In the process of preparing a compound of claim 1 the process comprising: refluxing a 2-halo-4,7,8,9-tetra-0-acyl-N-acyl neuraminic acid ester with HO.Flu in a reaction inert organic solvent capable of forming a solvent/water azeotrope in the presence of cadmium carbonate wherein acyl is alkanoyl of 1-5 carbon atoms or phenyl alkanoyl of 1-5 carbon atoms in the alkoxyl moiety, and halo is chloro, bromo or iodo.
Claim 9
Dependent Claim
20 words
The process of claim 7 wherein the reaction is carried out in a reaction inert organic solvent of b.p. 80°-200°C.
Claim 10
Dependent Claim
14 words
The process of claim 8 wherein the solvent is toluene or xylene, or mesitylene.
Claim 11
Dependent Claim
16 words
The process of claim 7 wherein acyl is acetyl, and the ester is a methyl ester.
Claim 12
Dependent Claim
14 words
The process of claim 10 wherein the solvent is toluene or xylene, or mesitylene.
Claim 13
Dependent Claim
23 words
A process of preparing 2-0-Flu-(N-acetyl-neuraminic acid) comprising: a. the process of claim 7, b. saponification of the 0-acyl moiety and the ester moiety.
Claim 14
Dependent Claim
17 words
A process of claim 12 wherein saponification is carried out by reaction with an alkali metal alkoxide.
Claim 15
Dependent Claim
24 words
A process of preparing 2-0-Flu-(N-acetyl-neuraminic acid) comprising: a. the process of claim 10, b. saponification of the 0-acetyl moiety and the methyl ester moiety.
Claim 16
Dependent Claim
17 words
A process of claim 14 wherein saponification is carried out by reaction with an alkali metal alkoxide.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-04-13 | 1979-10-13 | 1980-04-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-04-13 | 1983-10-13 | 1984-04-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-04-13 | 1987-10-13 | 1988-04-13 | $7700.00 | Window Closed / Lapsed |