Synthesis of new, base-modified PNA monomers

被引：3
|
作者：
Sipos, Ferenc [1 ]
Sagi, Gyula [1 ]
机构：
[1] Hungarian Acad Sci, Chem Res Ctr, Inst Biomol Chem, H-1025 Budapest, Hungary
来源：
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2007年 / 26卷 / 6-7期
关键词：
peptide nucleic acids; Pd-catalyzed cross-couplings; 5-substituted-uracils;
D O I：
10.1080/15257770701490613
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：
A number of N-Boc-protected peptide nucleic acids (PNA) monomers containing 5-aryl- and 5-alkynyl-uracil bases have been synthesized using different palladium-catalyzed cross-coupling reactions. Starting from the base-unprotected 5-iodo-uracil PNA monomer, only the Stille couplings were accomplished successfully, while Suzuki couplings with boronic acids containing the same aryl groups failed. During Sonogashira couplings with terminal alkynes, significant amounts of unrequired furano[2,3-d]pyrimidine by-products were formed. Protection of the lactam function by p-methosybenzylation prevented the opportunity for intramolecular cyclization as well as formation of a negative charge on the 4-O atom, making it possible to reach almost quantitative yields at Sonogashira couplings and acceptable conversions in Suzuki reactions.
引用
收藏
页码：681 / 685
页数：5
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