THE APPLICATION OF THE AMB PROTECTIVE GROUP IN THE SOLID-PHASE SYNTHESIS OF METHYLPHOSPHONATE DNA ANALOGS

被引：19

作者：

KUIJPERS, WHA ^{[1
]}

KUYLYEHESKIELY, E ^{[1
]}

VANBOOM, JH ^{[1
]}

VANBOECKEL, CAA ^{[1
]}

机构：

[1] GORLAEUS LABS,2300 RA LEIDEN,NETHERLANDS

来源：

NUCLEIC ACIDS RESEARCH | 1993年 / 21卷 / 15期

关键词：

D O I：

10.1093/nar/21.15.3493

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Partially methylphosphonate-modified oligodeoxynucleotides were synthesized on solid-phase by employing the easily removable 2-(acetoxymethyl)benzoyl (AMB) group as base-protecting group. Although a rapid AMB deprotection can be accomplished in methanolic potassium carbonate, the lability of the methylphosphonate linkage towards potassium carbonate/methanol excludes the use of this deprotection reagent. Thus, saturated ammonia solution in methanol was investigated as an alternative reagent for AMB removal. It is demonstrated that the combination of the AMB protective group and ammonia/methanol as deprotection reagent significantly improves the synthesis of methylphosphonate-modified DNA fragments. A mild overnight treatment at room temperature is sufficient for complete removal of the AMB group, whereas deprotection of conventionally protected oligonucleotides requires much longer exposure to basic conditions at elevated temperatures.

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页码：3493 / 3500

页数：8

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