Summary
Evaporation of a solution of thymidine plus either theexo or theendo diastereomer of uridine cyclic 2′,3′-O, O-phosphorothioate (U > p(S) in 1,2-diaminoethane hydrochloride buffer gave the 2′,5′ and 3′,5′ isomers of (P-thio) uridylylthymidine (Up(S)dT) in a ratio of 1:2 with a combined yield of about 20%. These isomers were re-converted to U > p(S) and dT by a reaction that is known to proceed by an in-line mechanism. Both the 2′,5′ and 3′,5′ isomers gave as product the same diastereomer of U > p(S) that had been used originally in their formation. These dry-state ‘prebiotic’ reactions (Verlander, Lohrmann, and Orgel 1973) are thus shown to be stereospecific, and both the 2′,5′ and 3′,5′ internucleotide bonds are formed by an in-line mechanism.
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Abbreviations
- DAE:
-
1,2-diaminoethane
- HPLC:
-
high pressure liquid chromatography
- RNase:
-
bovine pancreatic ribonuclease A, EC 3.1.4.22
- TEAB:
-
triethylammonium bicarbonate
- tris:
-
tris(hydroxymethyl)aminomethane
- UMP(S):
-
uridine monophosphorothioate
- U > p:
-
uridine cyclic 2′,3′-phosphate
- U > p(S):
-
uridine cyclic 2′,3′-O, O-phosphorothioate
- Up(S)dT:
-
(P-thio)uridylylthymidine
- U2′p(Rp-S)5′dT:
-
(P-thio)uridylylthymidine with theR configuration at phosphorous, and a 2′,5′ internucleotide linkage
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Usher, D.A., Yee, D. Geometry of the dry-state oligomerization of 2′,3′-cyclic phosphates. J Mol Evol 13, 287–293 (1979). https://doi.org/10.1007/BF01731369
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DOI: https://doi.org/10.1007/BF01731369