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Volumn 46, Issue 14, 2007, Pages 2470-2477

Mapping the landscape of potentially primordial informational oligomers: Oligodipeptides and oligodipeptoids tagged with triazines as recognition elements

Author keywords

Base pairing; DNA; Oligonucleotides; RNA; Triazines

Indexed keywords

DNA; PEPTIDES; REACTION KINETICS; RNA;

EID: 34250878397     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603207     Document Type: Article
Times cited : (84)

References (117)
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    • In the present context, an oligomer system is considered to be informational if it can accommodate constitutional diversity in the positioning of recognition elements such that any specific constitutional pattern of them can be read intermolecularly and (in principle) reproduced by self-replication
    • In the present context, an oligomer system is considered to be "informational" if it can accommodate constitutional diversity in the positioning of recognition elements such that any specific constitutional pattern of them can be "read" intermolecularly and (in principle) reproduced by self-replication.
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    • See also, however, the opposite viewpoint: a
    • See also, however, the opposite viewpoint: a) J. P. Ferris, Origins Life Evol. Biosphere 1993, 23, 307;
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    • Generational refers to generating a given molecule
    • Generational refers to generating a given molecule.
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    • What is to be meant as prebiotically realistic is and necessarily remains a matter of continuing debate, one that, however, can progressively be subjected to experimental scrutiny, for example, see: K. Nelson, M. Levy, S. L. Miller, Proc. Natl. Acad. Sci. 2000, 97, 3868
    • What is to be meant as prebiotically realistic is and necessarily remains a matter of continuing debate, one that, however, can progressively be subjected to experimental scrutiny, for example, see: K. Nelson, M. Levy, S. L. Miller, Proc. Natl. Acad. Sci. 2000, 97, 3868.
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    • See also, however, the opposite viewpoint in reference [16
    • See also, however, the opposite viewpoint in reference [16].
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    • Systematic contributions to nucleobase variation have been made by, The criteria for choosing nucleobase variants in these studies were different from those used in the present project
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    • [21c] have described the preparation a variety of 2,4-diaminotriazine derivatives by the reaction of morpholinobiguanide and dimethylbiguanide with α-amino acid esters.
    • [21c] have described the preparation a variety of 2,4-diaminotriazine derivatives by the reaction of morpholinobiguanide and dimethylbiguanide with α-amino acid esters.
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    • To include in our study peptoid oligomers as achiral variants of the di-aspartate derived oligomers of type B has been proposed by F.D.R, A.E
    • To include in our study peptoid oligomers as achiral variants of the di-aspartate derived oligomers of type B has been proposed by F.D.R. (A.E.).
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    • 13C NMR spectroscopy and mass spectrometry after purification by column chromatography on silica gel. Oligodipeptides and oligodipeptoids were synthesized on an Expedite 8909 Nucleic Acid Synthesizer (Perseptive Biosystems) using a modified PNA-protocol, purified by HPLC (ion exchange) to a minimal purity of 95% % and checked by MALDI-TOF-MS (see Supporting Information).
    • 13C NMR spectroscopy and mass spectrometry after purification by column chromatography on silica gel. Oligodipeptides and oligodipeptoids were synthesized on an Expedite 8909 Nucleic Acid Synthesizer (Perseptive Biosystems) using a modified PNA-protocol, purified by HPLC (ion exchange) to a minimal purity of 95% % and checked by MALDI-TOF-MS (see Supporting Information).
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    • It should be noted, however, that oligomer D(TN,N) 12 differs from the others carrying a positive charge in its backbone. We have not pursued further studies with this system because oligomers from this series were found to be constitutionally relatively unstable, lability of the backbone toward strandscission by β-elimination of the ammonium residue toward the α-position of the triazine ring, 37
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    • C. R. Cantor, P. R. Schimmel in Biophysical Chemistry, Freeman, San Francisco, CA, 1980, pp. 1135-1139; Part III (The Behavior of Biological Macromolecules).
    • C. R. Cantor, P. R. Schimmel in Biophysical Chemistry, Freeman, San Francisco, CA, 1980, pp. 1135-1139; Part III (The Behavior of Biological Macromolecules).
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    • m value has been reported in reference [24f].
    • m value has been reported in reference [24f].
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    • See the Supporting Information
    • See the Supporting Information.
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    • m value above 0°C.
    • m value above 0°C.
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    • m(UV) value.
    • m(UV) value.
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    • m = 14.4°C, c ≈ 5 + 5 μM, 1M NaCl).
    • m = 14.4°C, c ≈ 5 + 5 μM, 1M NaCl).
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    • TOO) because of temperature increments Measuring at 240 nm ensures observation of the change in absorption owing to the temperature dependence of a process (taken to be base pairing) different from nucleobase deprotonation.
    • TOO) because of temperature increments Measuring at 240 nm ensures observation of the change in absorption owing to the temperature dependence of a process (taken to be base pairing) different from nucleobase deprotonation.
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    • Angew. Chem. Int. Ed. 2007, 46, 2478.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.