Summary
We have synthesized 2′(3′)-O-(glycyl)-adenosine-5′-(O-methylphos-phate), an analogue of the 3′-terminus of aminoacylated tRNA. A 0.4M solution of this compound maintained at pH 8.2, yields 5.5% of diglycine and 11.5% of diketopiperazine, in addition to the hydrolysis products glycine and adenosine-5′-(O-methylphosphate). Under the same conditions, glycine ethyl ester reacts much more slowly, but ultimately gives similar yields of diglycine and diketopiperazine.
The aminolysis of 2′(3′)-O-(glycyl)-adenosine-5′-(O-methylphosphate) by free glycine is relatively inefficient, but serine reacts 20 times more rapidly and yields up to 50% of N-glycylserine. The prebiotic significance of these reactions is discussed.
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Abbreviations
- MepA:
-
adenosine-5′-(O-methylphosphate)
- MepA-gly:
-
2′(3′)-O-(glycyl)-adenosine-5′-(O-methylphosphate)
- MepA-bis-gly:
-
2′,3′-O-(bis-glycyl)-adenosine-5′-(O-methylphosphate)
- DKP:
-
diketopiperazine
- gly Et:
-
glycine ethyl ester
- gly-ser:
-
N-glycylserine
- O-gly-ser:
-
O-glycylserine
- O-(gly)-gly-ser:
-
O-(glycyl)-glycylserine
- Boc-gly:
-
N-tert-butyloxycarbonylglycine
- MepA-Boc-gly:
-
2′(3′)-O-(Boc-glycyl)-adenosine-5′-(O-methylphosphate)
- MepA-bis-Boc-gly:
-
2′,3′-O-(bis-Boc-glycyl)-adenosine-5′(O-methylphosphate)
- (gly)2 :
-
diglycine
- (gly)3 :
-
triglycine
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Weber, A.L., Orgel, L.E. The formation of peptides from the 2′(3′)-glycyl ester of a nucleotide. J Mol Evol 11, 189–198 (1978). https://doi.org/10.1007/BF01734480
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DOI: https://doi.org/10.1007/BF01734480