Další formáty:
BibTeX
LaTeX
RIS
@article{1383181,
author = {Xu, Jianfeng and Tsanakopoulou, Maria and Magnani, Christopher J. and Szabla, Rafal and Šponerová, Judit and Šponer, Jiří and Gora, Robert W. and Sutherland, John D.},
article_location = {London},
article_number = {4},
doi = {http://dx.doi.org/10.1038/NCHEM.2664},
keywords = {EXCITED-STATE; 2-THIOURACIL; PICTURE; DEACTIVATION; NUCLEOTIDES; NUCLEOSIDES; RELAXATION; PRECURSORS; CHEMISTRY; FORMAMIDE},
language = {eng},
issn = {1755-4330},
journal = {Nature chemistry},
title = {A prebiotically plausible synthesis of pyrimidine beta-ribonucleosides and their phosphate derivatives involving photoanomerization},
url = {https://www.nature.com/nchem/journal/v9/n4/full/nchem.2664.html},
volume = {9},
year = {2017}
}
TY - JOUR
ID - 1383181
AU - Xu, Jianfeng - Tsanakopoulou, Maria - Magnani, Christopher J. - Szabla, Rafal - Šponerová, Judit - Šponer, Jiří - Gora, Robert W. - Sutherland, John D.
PY - 2017
TI - A prebiotically plausible synthesis of pyrimidine beta-ribonucleosides and their phosphate derivatives involving photoanomerization
JF - Nature chemistry
VL - 9
IS - 4
SP - 303-309
EP - 303-309
PB - Nature Publishing Group
SN - 17554330
KW - EXCITED-STATE
KW - 2-THIOURACIL
KW - PICTURE
KW - DEACTIVATION
KW - NUCLEOTIDES
KW - NUCLEOSIDES
KW - RELAXATION
KW - PRECURSORS
KW - CHEMISTRY
KW - FORMAMIDE
UR - https://www.nature.com/nchem/journal/v9/n4/full/nchem.2664.html
L2 - https://www.nature.com/nchem/journal/v9/n4/full/nchem.2664.html
N2 - Previous research has identified ribose aminooxazoline as a potential intermediate in the prebiotic synthesis of the pyrimidine nucleotides with remarkable properties. It crystallizes spontaneously from reaction mixtures, with an enhanced enantiomeric excess if initially enantioenriched, which suggests that reservoirs of this compound might have accumulated on the early Earth in an optically pure form. Ribose aminooxazoline can be converted efficiently into alpha-ribocytidine by way of 2,2'-anhydroribocytidine, although anomerization to alpha-ribocytidine by ultraviolet irradiation is extremely inefficient. Our previous work demonstrated the synthesis of pyrimidine alpha-ribonucleotides, but at the cost of ignoring ribose aminooxazoline, using arabinose aminooxazoline instead. Here we describe a long-sought route through ribose aminooxazoline to the pyrimidine alpha-ribonucleosides and their phosphate derivatives that involves an extraordinarily efficient photoanomerization of alpha-2-thioribocytidine. In addition to the canonical nucleosides, our synthesis accesses alpha-2-thioribouridine, a modified nucleoside found in transfer RNA that enables both faster and more-accurate nucleic acid template-copying chemistry.
ER -
XU, Jianfeng, Maria TSANAKOPOULOU, Christopher J. MAGNANI, Rafal SZABLA, Judit ŠPONEROVÁ, Jiří ŠPONER, Robert W. GORA a John D. SUTHERLAND. A prebiotically plausible synthesis of pyrimidine beta-ribonucleosides and their phosphate derivatives involving photoanomerization. \textit{Nature chemistry}. London: Nature Publishing Group, 2017, roč.~9, č.~4, s.~303-309. ISSN~1755-4330. Dostupné z: https://dx.doi.org/10.1038/NCHEM.2664.
|
