US4266048A
Expired / Lapsed
US
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Synthesis of analogs of 3'-phosphoadenosine 5'-phosphosulfate (PAPS)
Assignee: United States Department of Health and Human Services
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Filing: 1978-10-26
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Granted: 1981-05-05
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Expires: 1998-10-26
Abstract
Abstract Analogs of 3'-phosphoadenosine 5'-phosphosulfate, also known as PAPS, are useful in establishing sulfate transfer mechanisms in animals and may be produced by a chemical process yielding an analog B of a pure adenosine 2',3'-cyclic phosphate 5'-phosphate, which compound is initially prepared from the reaction of adenosine and pyrophosphoryl chloride. In the present process an analog B is selected from 8-bromoadenine, purine, hypoxanthine, 4-aminopyrrolo[2,3-d]pyrimidine (tubercidin), and 7-amino-pyrazolopyrimidine (formycin). In the pilot procedure the pure cyclic phosphate is reacted with triethylamine-N-sulfonic acid to produce 2',3'-cyclic phosphate 5'-phosphosulfate. Subsequently, by hydrolysis with the enzyme ribonuclease-T2, the desired compound, an analog of PAPS, is produced. Alternatively, the 2'-phosphoadenosine 5'-phosphosulfate, known as iso-PAPS, may be produced from 2',3'-cyclic phosphate 5'-phosphosulfate by treatment with a different enzyme, PDase II or spleen phosphodiesterase.
Inventors
- 👤 Jerome P. Horwitz
- 👤 John P. Neenan
- 👤 Radhey S. Misra
- 👤 Jurij Rozhin
- 👤 Anne Huo
- 👤 Kerstin D. Philips, deceased
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 11:07
CPC Classifications
C; C12; C12P; C12P19/00; C12P19/26; C12P19/28; C12P19/30; C12P19/32; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/16; C07H19/20
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
64 words
A process for the preparation of ##STR7## ' -phospho B 5'-phosphosulfate where B is 8-bromoadenine, purine, hypoxanthine, 4-aminopyrrolo[2,3-d]pyrimidine (tubercidin), 7-aminopyrazolopyrimidine (formycin) by the reaction of ##STR8## and pyrophosphoryl chloride to produce a substantially pure ##STR9## B-2',3'-cyclic phosphate 5'-phosphate and subsequently reacting II with triethylamine-N-sulfonic acid to produce ##STR10## B 2',3'-cyclic phosphate 5'-phosphosulfate which is further treated with ribonuclease-T 2 to provide 3'-phospho B 5'-phosphosulfate.
Claim 2
Dependent Claim
64 words
A process for the preparation of ##STR7## ' -phospho B 5'-phosphosulfate where B is 8-bromoadenine, purine, hypoxanthine, 4-aminopyrrolo[2,3-d]pyrimidine (tubercidin), 7-aminopyrazolopyrimidine (formycin) by the reaction of ##STR8## and pyrophosphoryl chloride to produce a substantially pure ##STR9## B-2',3'-cyclic phosphate 5'-phosphate and subsequently reacting II with triethylamine-N-sulfonic acid to produce ##STR10## B 2',3'-cyclic phosphate 5'-phosphosulfate which is further treated with ribonuclease-T 2 to provide 3'-phospho B 5'-phosphosulfate.
Claim 3
Dependent Claim
25 words
A process in which Compound III (B 2',3'-cyclic phosphate 5'-phosphosulfate) is treated with the enzyme spleen PDase II to produce ##STR11## ' -phospho B 5'-phosphosulfate
Claim 4
Dependent Claim
25 words
A process in which Compound III (B 2',3'-cyclic phosphate 5'-phosphosulfate) is treated with the enzyme spleen PDase II to produce ##STR11## ' -phospho B 5'-phosphosulfate
Claim 5
Dependent Claim
38 words
The process according to claim 1 wherein the process is commenced with substantially pure pyrophosphoryl chloride II which is subsequently reacted with triethylamine-N-sulfonic acid and the product is subsequently treated with ribonuclease-T 2 to produce 3'-phospho B 5'-phosphosulfate.
Claim 6
Dependent Claim
27 words
A process of reacting Compound I with Compound II which is subsequently reacted with triethylamine-N-sulfonic acid and subsequently treated with spleen PDase to produce 2'-phospho B 5'-phosphosulfate.
Claim 7
Dependent Claim
27 words
A process of reacting Compound I with Compound II which is subsequently reacted with triethylamine-N-sulfonic acid and subsequently treated with spleen PDase to produce 2'-phospho B 5'-phosphosulfate.
Claim 8
Dependent Claim
75 words
The preparation of 2'-phospho B 5'-phosphosulfate (V) by a process reacting ##STR12## with pyrophosphoryl chloride to produce a pure B 2',3'-cyclic phosphate 5'-phosphate (II) and subsequently reacting said cyclic phosphate (II) with triethylamine-N-sulfonic acid to produce B 2',3'-cyclic phosphate 5'-phosphosulfate (III) and treating III with the enzyme spleen PDase to produce 2'-phospho B 5'-phosphosulfate (V) where B is selected from one member of the group consisting of 8-bromoadenine, purine, hypoxanthine, 4-aminopyrrolo[2,3-d]pyrimidine (tubercidin), and 7-aminopyrazolopyrimidine (formycin).
Claim 9
Dependent Claim
75 words
The preparation of 2'-phospho B 5'-phosphosulfate (V) by a process reacting ##STR12## with pyrophosphoryl chloride to produce a pure B 2',3'-cyclic phosphate 5'-phosphate (II) and subsequently reacting said cyclic phosphate (II) with triethylamine-N-sulfonic acid to produce B 2',3'-cyclic phosphate 5'-phosphosulfate (III) and treating III with the enzyme spleen PDase to produce 2'-phospho B 5'-phosphosulfate (V) where B is selected from one member of the group consisting of 8-bromoadenine, purine, hypoxanthine, 4-aminopyrrolo[2,3-d]pyrimidine (tubercidin), and 7-aminopyrazolopyrimidine (formycin).
References Cited (Backward Citations)
US3268416A
Cited
US4169011A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1984-05-04 | 1984-11-03 | 1985-05-05 | $2000.00 | Window Closed / Lapsed |
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