Summary
The self-condensation of 2′(3′)-O-glycyl esters of adenosine, adenosine-5′-(O-methylphosphate) and P1, P2-diadenosine-5′-pyrophosphate in 6.2 mM solutions at pH 8.0 and -5°C in the presence of 12.5 mM poly(U) yields approximately 3 times as much diketopiperazine as reactions without poly(U). As the concentration of 2′(3′)-O-(glycyl)-P1, P2-diadenosine-5′-pyrophosphate is decreased from 6.2 mM to 1.5 mM the yield of diketopiperazine in the presence of poly(U) decreases slightly from 6.6% to 5.2%, whereas, in the absence of poly(U) the yield of diketopiperazine decreases substantially from 2.4% to 0.75%. The enhanced yield of diketopiperazine that is attributed to the template action of poly(U) is temperature dependent and is observed only at temperatures below 10°C (5°C to -5°C) for 6.2 mM 2′(3′)-O-(glycyl)-adenosine-5′-(O-methylphosphate) and below 23°C (15°C to -5°C) for 6.2 mM 2′(3′)-O-(glycyl)-P1, P2-diadenosine-5′-pyrophosphate. The absence of a template effect at high temperatures is attributed to the melting of the organized helices. The hydrolysis half-lives at pH 8.0 and -5°C of 2′(3′)-O-(glycyl)-adenosine, 2′(3′)-O-(glycyl)-adenosine-5′-(O-methylphosphate), 2′(3′)-O-(glycyl)-P1, P2-diadenosine-5′-pyrophosphate, and 5′-O-(glycyl)-adenosine in the presence of poly(U) are substantially larger than their half-lives in the absence of poly(U). The condensation of 2′(3′)-O-(glycyl)-adenosine yields 5% of 5′-O-(glycyl)-adenosine in the presence of poly(U) compared to 0.7% in the absence of poly(U).
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Abbreviations
- DKP:
-
diketopiperazine
- (gly)2 :
-
glycylglycine
- (gly)3 :
-
glycylglycylglycine
- AppA-gly:
-
2′(3′)-O-(glycyl)-P1, P2-diadenosine-5′-pyrophosphate
- MepA-gly:
-
2′(3′)-O-(glycyl)-adenosine-5′-(O-methylphosphate)
- Ado-2′(3′)-gly:
-
2′(3′)-O-(glycyl)-adenosine
- Ado-5′-gly:
-
5′-O-(glycyl)-adenosine
- Boc-gly:
-
N-tert-butyloxycarbonylglycine
- AppA:
-
P1, P2-diadenosine-5′-pyrophosphate
- MepA:
-
adenosine-5′-(O-methylphosphate)
- AppA-Boc-gly:
-
2′(3′)-O-(Boc-glycyl)-P1, P2-diadenosine-5′-pyrophosphate
- Ado-5′-Boc-gly:
-
5′-O-(Boc-glycyl)-adenosine
- Ado-2′(3′)-Boc-gly:
-
2′(3′)-O-(Boc-glycyl)-adenosine
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Weber, A.L., Orgel, L.E. Poly(U)-directed peptide-bond formation from the 2′(3′)-glycyl esters of adenosine derivatives. J Mol Evol 16, 1–10 (1980). https://doi.org/10.1007/BF01732065
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DOI: https://doi.org/10.1007/BF01732065