93134-37-3Relevant articles and documents
METHOD FOR LIQUID-PHASE SYNTHESIS OF NUCLEIC ACID
-
Paragraph 0135; 0136; 0137, (2015/11/16)
In this method, an oligonucleotide is prepared by using, as a synthesis unit, a novel nucleoside monomer compound represented by formula (I) [wherein X, R1, Y, Base, Z, Ar, R2, R3 and n are each as defined in Claim 1]. The
Preparation of N3-thymidine-butylene-N3-thymidine interstrand cross-linked DNA via an orthogonal deprotection strategy
Sun, Gang,Noronha, Anne,Wilds, Christopher
experimental part, p. 7787 - 7793 (2012/09/25)
A DNA duplex containing an N3-thymidine-butylene-N3-thymidine interstrand cross-link (ICL) was prepared using an on-column orthogonal deprotection strategy to permit different nucleotide sequence composition around the cross-linked site. The conditions us
Biodegradable protections for nucleoside 5′-monophosphates: Comparative study on the removal of O-acetyl and O-acetyloxymethyl protected 3-hydroxy-2,2-bis(ethoxycarbonyl)propyl groups
Ora, Mikko,Taherpour, Sharmin,Linna, Risto,Leisvuori, Anna,Hietamaeki, Emilia,Poijaervi-Virta, Paeivi,Beigelman, Leonid,Loennberg, Harri
experimental part, p. 4992 - 5001 (2009/10/17)
(Chemical Equation Presented) The applicability of 3-acetyloxy-2,2- bis(ethoxycarbonyl)propyl and 3-acetyloxymethoxy-2,2-bis(ethoxycarbonyl) propyl groups as biodegradable phosphate protecting groups for nucleoside 5′-monophosphates has been studied in a HEPES buffer at pH 7.5. Enzymatic deacetylation with porcine carboxyesterase triggers the removal of the resulting 3-hydroxy-2,2-bis(ethoxycarbonyl)propyl and 3-hydroxymethoxy-2,2- bis(ethoxycarbonyl)propyl groups by retro-aldol condensation and consecutive half acetal hydrolysis and retro-aldol condensation, respectively. The kinetics of these multistep deprotection reactions have been followed by HPLC, using appropriately protected thymidine 5′-monophosphates as model compounds. The enzymatic deacetylation of the 3-acetyloxymethoxy-2,2-bis(ethoxycarbonyl) propyl 5′-triester (2) is 25-fold faster than the deacetylation of its 3-acetyloxy-2,2-bis(ethoxycarbonyl)propyl-protected counterpart 1, and the difference in the deacetylation rates of the resulting diesters, 12b and 12a, is even greater. With 2, conversion to thymidine 5′-monophosphate (5′-TMP) is quantitative, while conversion of 1 to 5′-TMP is accompanied by formation of thymidine. Consistent with the preceding observations, quantitative release of 5′-TMP from 2 has been shown to take place in a whole cell extract of human prostate cancer cells.