Porphyrin substituted phosphoramidites: new building blocks for porphyrin-oligonucleotide syntheses

被引：39

作者：

Balaz, M ^{[1
]}

Holmes, AE ^{[1
]}

Benedetti, M ^{[1
]}

Proni, G ^{[1
]}

Berova, N ^{[1
]}

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2005年 / 13卷 / 07期

关键词：

porphyrin; automated oligonucleotide synthesis; modified oligonucleotide; DNA synthesis; purification;

D O I：

10.1016/j.bmc.2005.01.045

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：

Thymidine phosphoramidites containing trispyridylphenyl and tetraphenylporphyrin chromophores attached via a short amide linker in the 3'-position have been synthesized and used as building blocks in solid-phase synthesis of self-complementary 8-mer oligonucleotides 3'-T-5'-GCGCGCA-3' and 5'-ACGCGCGT-3'. To our knowledge, these are the first porphyrin-oligonucleotide conjugates carrying the porphyrin chromophores in the 3'-position. Chain assembly was achieved by automated solid-phase synthesis and by inexpensive straightforward `in flask' modification of commercially available solid supported oligonucleotides. This approach allows the synthesis of modified oligonucleotides without using costly instrumentation for automated DNA synthesis. Porphyrin-containing self-complementary oligonucleotides are expected to be a valuable model for drug binding studies and determination of conformational changes in DNA sequences using circular dichroism. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2413 / 2421

页数：9