SYNTHESIS OF PEPTIDE NUCLEIC-ACID MONOMERS CONTAINING THE 4 NATURAL NUCLEOBASES - THYMINE, CYTOSINE, ADENINE, AND GUANINE AND THEIR OLIGOMERIZATION
SYNTHESIS OF PEPTIDE NUCLEIC-ACID MONOMERS CONTAINING THE 4 NATURAL NUCLEOBASES - THYMINE, CYTOSINE, ADENINE, AND GUANINE AND THEIR OLIGOMERIZATION
复制标题
DOI：
10.1021/jo00098a042
复制
发表时间：
1994-09-23
影响因子：
3.6
通讯作者：
BUCHARDT, O
中科院分区：
文献类型：
--
作者：
DUEHOLM, KL;EGHOLM, M;BUCHARDT, O
本文介绍了混合序列PNA（含有胸腺嘧啶、胞嘧啶、腺嘌呤和鸟嘌呤四种天然核碱基的PNA）的制备方法。通过会聚合成法制备了含有胸腺嘧啶、Cbz保护的胞嘧啶、腺嘌呤或苄基保护的鸟嘌呤的PNA单体。在嘧啶的N-1或嘌呤的N-9处引入羧甲基连接基并适当保护环外基团之后，将核碱基衍生物偶联到Boc保护的骨架酯10a或10 b上，并最终水解，得到单体12 a-d。胞嘧啶和腺嘌呤的环外氨基用苄氧羰基保护。鸟嘌呤的环外氨基未被保护，而O-6被保护为苄基醚。基本上按照标准固相肽合成方案组装两个混合序列10聚体，每个都掺入了五个嘌呤，和一个含有七个嘌呤的混合序列15聚体。
The preparation of mixed-sequence PNAs (PNAs containing the four natural nucleobases; thymine, cytosine, adenine, and guanine) is described. The PNA monomers containing thymine, Cbz-protected cytosine, or adenine or benzyl-protected guanine were prepared via convergent syntheses. Subsequent to introduction of the carboxymethyl linker at N-1 of the pyrimidines or N-9 of the purines and suitable protection of exocyclic groups, the nucleobase derivatives were coupled to the Boc-protected backbone esters 10a or 10b and finally hydrolyzed affording the monomers 12a-d. The exocyclic amino groups of cytosine and adenine were protected with a benzyloxycarbonyl group. The exocyclic amino group of guanine was left unprotected whereas O-6 was protected as the benzyl ether. Two mixed-sequence 10-mers, each with five purines incorporated, and a mixed-sequence 15-mer Containing seven purines were assembled essentially following standard solid phase peptide synthesis protocols.