452-51-7Relevant articles and documents
Prebiotic phosphorylation of 2-thiouridine provides either nucleotides or DNA building blocks via photoreduction
Xu, Jianfeng,Green, Nicholas J.,Gibard, Clémentine,Krishnamurthy, Ramanarayanan,Sutherland, John D.
, p. 457 - 462 (2019/04/08)
Breakthroughs in the study of the origin of life have demonstrated how some of the building blocks essential to biology could have been formed under various primordial scenarios, and could therefore have contributed to the chemical evolution of life. Missing building blocks are then sometimes inferred to be products of primitive biosynthesis, which can stretch the limits of plausibility. Here, we demonstrate the synthesis of 2′-deoxy-2-thiouridine, and subsequently 2′-deoxyadenosine and 2-deoxyribose, under prebiotic conditions. 2′-Deoxy-2-thiouridine is produced by photoreduction of 2,2′-anhydro-2-thiouridine, which is in turn formed by phosphorylation of 2-thiouridine—an intermediate of prebiotic RNA synthesis. 2′-Deoxy-2-thiouridine is an effective deoxyribosylating agent and may have functioned as such in either abiotic or proto-enzyme-catalysed pathways to DNA, as demonstrated by its conversion to 2′-deoxyadenosine by reaction with adenine, and 2-deoxyribose by hydrolysis. An alternative prebiotic phosphorylation of 2-thiouridine leads to the formation of its 5′-phosphate, showing that hypotheses in which 2-thiouridine was a key component of early RNA sequences are within the bounds of synthetic credibility.
A 2-deoxy-D-ribose preparation method
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Paragraph 0067; 0076; 0077, (2019/02/02)
The invention discloses a preparation method of 2-deoxidation-D-ribose. The method comprises the following steps: (1) carrying out a Reformasky reaction on D-glyceraldehyde acetonide and ethyl bromoacetate at an inert atmosphere and under a catalytic action of active zinc powder so as to obtain a compound shown in the formula I; (2) carrying out a substitution reaction on the compound shown in the formula I and an organic silicon protecting agent in the presence of an alkali so as to obtain a compound shown in the formula II; (3) carrying out a reduction reaction on the compound shown in the formula II under the condition of a reducing agent so as to obtain a compound shown in the formula III; (4) carrying out an oxidation reaction on the compound shown in the formula III under the condition of an oxidizing agent so as to obtain a compound shown in the formula IV; (5) carrying out deprotection on the compound shown in the formula IV in the presence of an acid and then carrying out a cyclization reaction so as to obtain the 2-deoxidation-D-ribose. According to the method, the Reformasky reaction is adopted, so that the selectivity is good; the high-yield compound shown in the formula I is obtained. The method is convenient to operate, low in raw material cost and easy to industrialize.
A new synthetic strategy for 2-deoxy-D-ribose via palladium(II)-catalyzed cyclization of aldehyde
Miyazawa, Masahiro,Awasaguchi, Ken-Ichiro,Uoya, Ikuyo,Yokoyama, Hajime,Hirai, Yoshiro
, p. 1891 - 1902 (2011/04/12)
We achieved a total synthesis of 2-deoxy-D-ribose through intramolecular Pd(II)-catalyzed cyclization of aldehyde via an unstable hemiacetal intermediate as a key step. The Japan Institute of Heterocyclic Chemistry.
