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EP0251786A2
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Alkynylamino-nucleotides
Assignee: Revvity Health Sciences Inc
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Filing: 1987-07-01
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Granted: —
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Expires: 2007-07-01
Abstract
Abstract The invention provides alkynylamino-nucleotides and their labeled derivatives which are useful, for example, as chain terminating substrates for DNA sequencing, along with several key intermediates and processes for their preparation.
Inventors
- 👤 George Leonard Trainor
- 👤 Frank Worden Hobbs, Jr.
- 👤 Anthony Joseph Cocuzza
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-30 06:37
CPC Classifications
C; C07; C07H; C07H21/00; C07H21/04; C07D; C07D405/00; C07D405/02; C07D405/04; C07D405/12; C07D405/14; C07D471/00; C07D471/02; C07D471/04; C07D487/00; C07D487/02; C07D487/04; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/645; C07F9/6509; C07F9/6512; C07F9/6558; C07F9/65586; C07F9/6561; C07H19/00; C07H19/02; C07H19/04; C07H19/06; C07H19/10; C07H19/16; C07H19/20; C12; C12Q; C12Q1/00; C12Q1/68; C12Q1/6869; G; G01; G01N; G01N27/00; G01N27/26; G01N27/416; G01N27/447; G01N27/44704; G01N27/44717; G01N27/44721; G01N27/44726
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
72 words
An alkynylamino-nucleotide having the structure: Nuc-C≡C-R₁-NR₂R₃ wherein R₁ is a diradical moiety of 1-20 atoms. R₂ and R₃ are, independently, H, C₁-C₄ alkyl or a protecting group, and Nuc is R₄-Het having the structure wherein R₅ is H, PO₃H₂, P₂O₆H₃, P₃O₉H₄ or salts thereof, and (i) when R₇=R₈=H, then R₆=H, OH, F, N₃ or NH₂; or (ii) when R₇=H and R₈-OH, then R₆-H or OH; or (iii)when R₇=OH and R₈=H, then R₆=OH.
Claim 2
Dependent Claim
72 words
An alkynylamino-nucleotide having the structure: Nuc-C≡C-R₁-NR₂R₃ wherein R₁ is a diradical moiety of 1-20 atoms. R₂ and R₃ are, independently, H, C₁-C₄ alkyl or a protecting group, and Nuc is R₄-Het having the structure wherein R₅ is H, PO₃H₂, P₂O₆H₃, P₃O₉H₄ or salts thereof, and (i) when R₇=R₈=H, then R₆=H, OH, F, N₃ or NH₂; or (ii) when R₇=H and R₈-OH, then R₆-H or OH; or (iii)when R₇=OH and R₈=H, then R₆=OH.
Claim 3
Dependent Claim
15 words
An alkynylamino nucleotide according to claim 1 wherein R₁ is straight chained C₁-C₁₀ alkylene moiety.
Claim 4
Dependent Claim
10 words
An alkynylamino nucleotide according to claim 2 wherein R₁ is-CH₂-.
Claim 5
Dependent Claim
22 words
An alkynylamino nucleotide according to claim 1, 2 or 3 wherein R₂ is H and R₃ is H or a protecting group.
Claim 6
Dependent Claim
16 words
An alkynylamino-nucleotide according to any one of the preceding claims wherein R₄ is a chain-terminating sugar.
Claim 7
Dependent Claim
21 words
A labeled alkynylamino-nucleotide wherein R₃ in an alkynylamino-nucleotide as claimed in any one of the preceding claims is a reporter group.
Claim 8
Dependent Claim
13 words
A labeled alkynylamino-nucleotide according to claim 6 wherein R₃ is a fluorescent group.
Claim 9
Dependent Claim
22 words
A process for preparing 2-thioalkoxy-6-alkoxy-7-iodo-7-deazapurines including the step of treating 2-thioalkoxy-6-alkoxy-7-deazapurines with N-iodosuccinimide for the regioselective introduction of iodine at the 7-position.
Claim 10
Dependent Claim
22 words
A process for preparing 2-thioalkoxy-6-alkoxy-7-iodo-7-deazapurines including the step of treating 2-thioalkoxy-6-alkoxy-7-deazapurines with N-iodosuccinimide for the regioselective introduction of iodine at the 7-position.
Claim 11
Dependent Claim
141 words
A process of preparing 7-(3-amino-1-propynyl)-2ʹ,3ʹ-dideoxyguanosine 5ʹ-triphosphate comprising the steps of: (A) contacting 6-methoxy-2-methylthio-7-deazapurine with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-ribofuranose in presence of sodium hydride; (B) hydrolyzing the ester product 9 of step (A) under basic condition to diol 10 ; (C) protecting the 5-OH position in diol 10 with a trityl group; (D) removing the 3-OH group by reducing an intermediate thionocarbonate with a tin hydride reducing agent; (E) treating the dideoxydeazapurine 12 resulting from step (D) with N-iodosuccinimide to form the 7-iodo derivative 13 ; (F) contacting compound 13 with sodium thiocresolate in hexamethylphosphoramide to form the 7-deazapurin-6-one 14 ; (G) treating compound 14 successively with meta-chloroperoxybenzoic acid and ammonia to obtain the 7-deazaguanosine 15 ; (H) coupling N-propargyltrifluoroacetamide to the deprotected 7-iodo compound 16 to obtain 7-(3-trifluoroacetamido-1-propynyl)-2ʹ,3ʹ-dideoxy 7-deazaguanosine; and (I) converting the product of step (H) to the 5ʹ triphosphate followed by deprotection.
Claim 12
Dependent Claim
141 words
A process of preparing 7-(3-amino-1-propynyl)-2ʹ,3ʹ-dideoxyguanosine 5ʹ-triphosphate comprising the steps of: (A) contacting 6-methoxy-2-methylthio-7-deazapurine with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-ribofuranose in presence of sodium hydride; (B) hydrolyzing the ester product 9 of step (A) under basic condition to diol 10 ; (C) protecting the 5-OH position in diol 10 with a trityl group; (D) removing the 3-OH group by reducing an intermediate thionocarbonate with a tin hydride reducing agent; (E) treating the dideoxydeazapurine 12 resulting from step (D) with N-iodosuccinimide to form the 7-iodo derivative 13 ; (F) contacting compound 13 with sodium thiocresolate in hexamethylphosphoramide to form the 7-deazapurin-6-one 14 ; (G) treating compound 14 successively with meta-chloroperoxybenzoic acid and ammonia to obtain the 7-deazaguanosine 15 ; (H) coupling N-propargyltrifluoroacetamide to the deprotected 7-iodo compound 16 to obtain 7-(3-trifluoroacetamido-1-propynyl)-2ʹ,3ʹ-dideoxy 7-deazaguanosine; and (I) converting the product of step (H) to the 5ʹ triphosphate followed by deprotection.
Claim 13
Dependent Claim
23 words
A process for preparing 6-chloro-7-iodo-7-deazapurines including the step of treating 6-chloro-7-deazapurines with iodine monochloride for the regioselective introduction of iodine at the 7-position.
Claim 14
Dependent Claim
23 words
A process for preparing 6-chloro-7-iodo-7-deazapurines including the step of treating 6-chloro-7-deazapurines with iodine monochloride for the regioselective introduction of iodine at the 7-position.
Claim 15
Independent Claim
42 words
A method for preparing alkynylamino-nucleotides by coupling iodo-nucleotides having an iodine atom attached to a carbon atom within the heterocyclic base with terminal alkynyl amines using a bis(triphenylphosphine) palladium dichloride/cuprous iodide catalyst, characterised by the use of a tetrakis(triphenylphosphine)palladium(O)/ cuprous iodide catalyst.
Claim 16
Independent Claim
42 words
A method for preparing alkynylamino-nucleotides by coupling iodo-nucleotides having an iodine atom attached to a carbon atom within the heterocyclic base with terminal alkynyl amines using a bis(triphenylphosphine) palladium dichloride/cuprous iodide catalyst, characterised by the use of a tetrakis(triphenylphosphine)palladium(O)/ cuprous iodide catalyst.
Claim 17
Dependent Claim
14 words
7-Iodo-nucleotides having the structure: wherein Z and R₄ are as defined in claim 1.
References Cited (Backward Citations)
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