JP2008069181A - 合成用の改良されたシントンと、緩やかな条件下でのペプチド核酸の保護解除方法 - Google Patents

合成用の改良されたシントンと、緩やかな条件下でのペプチド核酸の保護解除方法 Download PDF

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JP2008069181A
JP2008069181A JP2007315280A JP2007315280A JP2008069181A JP 2008069181 A JP2008069181 A JP 2008069181A JP 2007315280 A JP2007315280 A JP 2007315280A JP 2007315280 A JP2007315280 A JP 2007315280A JP 2008069181 A JP2008069181 A JP 2008069181A
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compound
carbamate
protected
synthon
protected nucleobase
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James M Coull
エム． コウル ジェームズ
Michael Egholm
エゴーム マイケル
Richard P Hodge
ピー． ホッジ リチャード
Mohamed Ismail
イスメイル モハメド
S B Rajur
ビー． ラジュア エス．
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Applied Biosystems LLC
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PerSeptive Biosystems Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
    • C07D473/32—Nitrogen atom
    • C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/001—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof by chemical synthesis
    • C07K14/003—Peptide-nucleic acids (PNAs)
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Gastroenterology & Hepatology (AREA)
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Abstract

【課題】従来技術の課題を克服する新規ＰＮＡシントンの合成方法の提供。
【解決手段】(a)〜(e)の段階からなるカーバメート保護された核酸塩基側鎖部分の合成方法：(a) 環外アミノ基と複素環Ｎ−原子とを有する部分的に保護された核酸塩基化合物を合成し(b) この部分的に保護された核酸塩基化合物の環外アミノ基を電子親和性を有するカルボニル均等物と反応させてN-置換中間化合物を合成し(c) この中間化合物をアルコールと反応させてカーバメート保護アミノ基を有する完全に保護された核酸塩基化合物を合成し(d) この完全保護された核酸塩基化合物を金属アルコキシドまたは金属水酸化物と反応させてカーバメート保護された核酸塩基側鎖部分の金属塩を合成しこの金属塩は主鎖カルボン酸基を有し(e) この主鎖カルボン酸基または複素環N-原子のプロトン付加に適した条件で酸を用いて、カーバメート保護された核酸塩基側鎖部分を得る。
【選択図】なし

Description

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図１は本発明のグアニンＰＮＡシントンの合成スキーム。 図２は本発明の好ましいグアニンＰＮＡシントンの合成スキーム。 図３は本発明の好ましいアデニンＰＮＡシントンの合成スキーム。 図４は本発明の好ましいシトシンＰＮＡシントンの合成スキーム。 図５は本発明で有用な天然または非天然の核酸塩基の構造を示したチャート。 図６はＰＮＡオリゴマー配列Fmoc-CAGGAGTCGCAT-gly-NH2のＨＰＬＣトレース。

Claims (1)

  1. 本願明細書等に記載されるような、核酸の保護解除方法。
JP2007315280A 1995-06-07 2007-12-05 合成用の改良されたシントンと、緩やかな条件下でのペプチド核酸の保護解除方法 Withdrawn JP2008069181A (ja)

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US08/487,666 US6133444A (en) 1993-12-22 1995-06-07 Synthons for the synthesis and deprotection of peptide nucleic acids under mild conditions

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DE (1) DE69638047D1 (ja)
WO (1) WO1996040685A1 (ja)

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JPH11507911A (ja) 1999-07-13
US6172226B1 (en) 2001-01-09
US6133444A (en) 2000-10-17
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