A Fmoc-based submonomeric strategy for the solid phase synthesis of optically pure chiral PNAs

被引：5

作者：

Tedeschi, Tullia ^{[1
]}

Sforza, Stefano ^{[1
]}

Maffei, Francesca ^{[1
]}

Corradini, Roberto ^{[1
]}

Marchelli, Rosangela ^{[1
]}

机构：

[1] Univ Parma, Dipartimento Chim Organ & Ind, I-43100 Parma, Italy

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 33期

关键词：

chiral PNAs; submonomeric strategy; optical purity; Fmoc strategy;

D O I：

10.1016/j.tetlet.2008.05.114

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new submonomeric approach for the Fmoc solid phase synthesis of chiral PNAs is reported here. The design and synthesis of a new D-lysine-based Fmoc submonomer obtained by replacing the nucleobase residue with an Alloc group, compatible with Fmoc chemistry, is described starting from D-lysine and Fmoc-aminoacetaldehyde. The desired submonomer was obtained in high yield with no racemization. The conditions for synthesizing a chiral PNA dimer on solid support by a submonomeric approach have been optimized, allowing to obtain the desired PNA with a very high optical purity. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：4958 / 4961

页数：4

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