Title of article :
Synthesis of novel exocyclic amino nucleosides by parallel solid-phase combinatorial strategy
Author/Authors :
Chamakura V.N.S. Varaprasad، نويسنده , , Qazi Habib، نويسنده , , David Y Li، نويسنده , , Jingfan Huang، نويسنده , , Jeffrey W Abt، نويسنده , , Frank Rong، نويسنده , , Zhi Hong، نويسنده , , Haoyun An، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2003
Pages :
11
From page :
2297
To page :
2307
Abstract :
A versatile parallel solid-phase combinatorial strategy was developed for the synthesis of large nucleoside libraries. Twelve libraries of 1152 novel exocyclic triazinylamino nucleosides and one library of 82 new substituted clitocine derivatives were synthesized in high quality as natural product mimic nucleosides on the semi-automated synthesizer. The polystyrene MMT-Cl resin was selected and utilized. The key intermediate resins and loaded with the corresponding scaffolds were prepared and validated with various amines before parallel synthesis. After a variety of amino building blocks were validated, 56 primary amines in 12 groups (building block set A) and 24 secondary amines in 3 groups (building block set B) were selected and utilized to combinatorialize the first and the second reactive sites on scaffold for the synthesis of libraries . Eighty-two amines (building block set C) were utilized for the synthesis of clitocine library . Thirteen libraries of 1234 novel exocyclic amino nucleosides were all analyzed and characterized by high throughput LC-MS. 81.3–100% of the library members in 13 libraries show more than 60% purity, and 65.7–92.7% of the library members in these libraries show 80–100% purity. The strategy can be widely used for the synthesis of other diverse nucleoside libraries.
Keywords :
exocyclic amino nucleoside , triazinyl , clitocine mimic , parallel solid-phase combinatorial , Library , Automated synthesis
Journal title :
Tetrahedron
Serial Year :
2003
Journal title :
Tetrahedron
Record number :
1087647
Link To Document :
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