1440632-75-6

Upstream product

• 504-57-4 10-Nonadecanon 
• 1463-10-1 5-Methyluridine 
• 24163-93-7 farnesyl bromide 
• 1440632-40-5 1-(6-hydroxymethyl-2,2-dinonyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-5-methyl-1H-pyrimidin-2,4-dione 

Relevant academic research and scientific papers

REACTIVE, LIPOPHILIC NUCLEOSIDE BUILDING BLOCKS FOR THE SYNTHESIS OF HYDROPHOBIC NUCLEIC ACIDS

The present invention relates to a method for the isolation and/or identification of known or unknown sequences of nucleic acids (target sequences) optionally marked with reporter groups by base specific hybridation with complementary sequences using nucleolipids. The nucleolipids are prepared by lipophilizing nucleosides of formula (Ia) wherein Q represents a group having a substituted tetrahydrofuran ring and Bas represents a group having one or more heterocyclic rings having one or more heterocyclic nitrogen atoms.

Reactive, lipophilic nucleoside building blocks for the synthesis of hydrophobic nucleic acids

The present invention relates to a method for the isolation and/or identification of known or unknown sequences of nucleic acids (target sequences) optionally marked with reporter groups by base specific hybridation with, essentially, complementary sequences (in the following referred to as sample oligonucleotides, sample sequences or sample nucleic acids), which belong to a library of sequences. Further, the invention relates to nucleolipids used in the method of the invention and a process for the preparation of said nucleolipids.

Synthesis of thymidine, uridine, and 5-methyluridine nucleolipids: Tools for a tuned lipophilization of oligonucleotides

Three pyrimidine nucleosides, uridine (1), 5-methyluridine (6), and 2′-deoxythymidine (11), were converted to amphiphilic nucleolipids. Compounds 1 and 6 were lipophilized by introduction of symmetric ketal moieties with various carbon chain lengths (i.e., 5-17). Two ketal derivatives, 2b and 7a, were additionally further hydrophobized by N(3)-farnesylation. 2′-Deoxythymidine was alkylated at N(3) with a cetyl (=hexadecyl) residue, either directly or, after complete orthogonal protection of the sugar OH groups, by Mitsunobu reaction with hexadecan-1-ol. Some of the nucleolipids were subsequently converted to their 2-cyanoethyl phosphoramidites (5′ or 3′), one of which was used for an exemplary synthesis of a lipo-oligonucleotide. The sequence of this lipo-oligonucleotide is an encoded manifestation of Pythagoras' law, created with a key table in which the letters of the alphabet, the numbers from 0 to 9 as well as the mostly used mathematical symbols are allocated to a ribonucleic acid triplet of the genetic code. Copyright