The Stereochemical Basis of Template Function

Rackwitz, Hans Richard; Scheit, K. H.

doi:10.1111/j.1432-1033.1977.tb11239.x

Cited by 36 publications

(39 citation statements)

References 23 publications

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“…In agreement with the latter analogy, the 5'-triphosphate derivative of the 2-aminopurine nucleoside is reported to function exclusively as an adenosine analogue in at least one enzymatic process (20). The possibility that 2-aminopurine could base pair with either thymine or cytosine has been suggested to account for its strong mutagenic properties (21).…”

Section: Introductionmentioning

confidence: 49%

A new approach to the synthesis of a protected 2-aminopurine derivative and its incorporation into oligodeoxynucleotides containing the Eco RI and Bam HI recognition sites

et al. 1988

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A protected 2-aminopurine nucleoside suitable for incorporation into oligodeoxynucleotides using phosphite triester chemical synthesis procedures has been prepared via oxidation of a purine hydrazino derivative with silver (I) oxide. Five oligodeoxynucleotides containing Eco RI and Bam HI recognition sites have been prepared such that, in the double stranded form, the 2-aminopurine base has either a complementary thymine or cytosine nucleobase. The helix character and thermodynamic parameters for helix formation have been examined.

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Section: Introductionmentioning

confidence: 49%

A new approach to the synthesis of a protected 2-aminopurine derivative and its incorporation into oligodeoxynucleotides containing the Eco RI and Bam HI recognition sites

et al. 1988

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“…All these methods, but also standard procedures like the polymerase chain reaction, for instance, would gain from an improvement in duplex stability of oligonucleotides. A way to achieve this is the substitution of natural nucleotides by base modifications, like pyrimidines with a halogen at the C 5-position, which reportedly influences the base stacking [5], and 2,6-diaminopurine with a third hydrogen bond in its base pairing with thymine [6,7] which is known to thermally stabilize DNA-duplexes [8,9]. Since both 2,6-diaminopurine and 5-chloro-uracil 2' -deoxynucleosides are not available as phosphoramidites for a standard chemical synthesis of oligonucleotides, their 5'-Correspondence address: J.D.…”

Section: Introductionmentioning

confidence: 99%

Quantitative measurements on the duplex stability of 2,6‐diaminopurine and 5‐chloro‐uracil nucleotides using enzymatically synthesized oligomers

1990

FEBS Letters

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2,6‐Diaminopurine and 5‐chloro‐uracil 2'‐deoxynucleoside 5'‐triphosphates were synthesized from their 2'‐deoxynucleosides. Using a method of creating oligonucleotides by enzymatic primer extension, dodecanucleotides representing an XbaI/SalI site and the complementary SalI/XbaI site were generated containing these base modifications. Their duplex stability was quantitatively compared by thin‐layer chromatography to oligomers containing 2'‐deoxyadenosine and 2'‐deoxythymidine. The two unmodified oligomers already showed significant differences in dissociation temperature and binding equilibrium. Substitution with 5‐chloro‐2'‐deoxyuridine did not affect the dissociation temperature of either oligomer, the 2,6‐diaminopurine, however, led to an increase of 1.8°C or 1.5°C per modified base, respectively. While in the XbaI/SalI oligomer both base modifications changed the binding equilibrium, the 2,6‐diaminopurine by a factor of 1.32, the 5‐chloro‐uracil by 0.65, no such effect was found with the complementary oligomer.

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“…We shall emphasize the importance of considering the specific nature of the genetic transition (i.e., A-T--'G-C or G-C-"A.T) that one assays when interpreting mutagenesis data. Each of the two effects of BrdUrd treatment is expected to preferentially induce one type of transition, and we analyze the ability of normal deoxyribonucleosides to act both as synergists and counteragents when added during BrdUrd mutagenesis.We will also explain how the inhibition of adenosine deaminase (9, 27) by APur-deoxyribose leads us to predict that the mutagenic effects of APur are also 2-fold: perturbation of normal deoxyribonucleoside triphosphate pool sizes and the well-documented base-pairing ambiguities (9,12,(28)(29)(30)(31)(32)(33).Abbreviations: BrUra, 5-bromouracil; APur, 2-aminopurine; ADAase, adenosine deaminase. …”

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confidence: 99%

“…We will also explain how the inhibition of adenosine deaminase (9,27) by APur-deoxyribose leads us to predict that the mutagenic effects of APur are also 2-fold: perturbation of normal deoxyribonucleoside triphosphate pool sizes and the well-documented base-pairing ambiguities (9,12,(28)(29)(30)(31)(32)(33) Biochemistry: Hopkins and Goodman A second topic regarding APur and BrdUrd mutagenesis will be discussed: their antipolarity. There seems to be conflicting evidence concerning whether BrUra and APur preferentially induce A-T-G-C transitions more frequently than G-C-A-T transitions or vice versa (8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21).…”

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Deoxyribonucleotide pools, base pairing, and sequence configuration affecting bromodeoxyuridine- and 2-aminopurine-induced mutagenesis.

Hopkins¹,

Goodman²

1980

Proc. Natl. Acad. Sci. U.S.A.

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Despite recent experiments showing that BrdUrd-induced mutagenesis can be independent of the level of bromouracil (BrUra) 5-Bromouracil (BrUra), an analogue of thymine, and 2-aminopurine (APur), an analogue of adenine, cause transition mutations in various organisms (1-14). A-T--'G-C and G-C oA-T transitions are induced by both base analogues; however, the extent of their bidirectionality remains unclear (8-21). It is known that BrUra and APur are incorporated "normally" into DNA opposite adenine and thymine, respectively. Ambiguities in their base pairing properties (BrUra can pair with guanine and APur with cytosine) are clearly important determinants in their mutagenicity and lead to what Freese (9) and Rudner (19) defined as replication errors and incorporation errors.Under certain conditions, BrUra substitution in DNA is not correlated with BrdUrd mutagenesis. This point was forcefully made in recent experiments by Kaufman and Davidson (22) using Syrian hamster melanoma cells and by Aebersold using Chinese hamster cells (1). For example, in the Kaufman and Davidson experiment it was shown that BrdUrd-induced mutation frequencies in a Syrian hamster melanoma cell line depended not on how much BrUra was stably substituted for thymine in the DNA but rather on the concentration of BrdUrd in the cell growth medium. In view of the evidence in Salmonella (14) and in bacteriophage T4 (23), which supports the idea that BrUra increases replication errors when acting in a template capacity, the Syrian hamster melanoma results are remarkable, to say the least.The publication costs of this article were defrayed in part by page charge payment. This article must therefore be hereby marked "advertisement" in accordance with 18 U. S. C. §1734 solely to indicate this fact. 1801It will be of fundamental importance in understanding the mechanism of BrdUrd mutagenesis to recognize that the uncoupling of the level of BrUra substitution in DNA from the level of BrdUrd mutagenesis was achieved through the addition of deoxythymidine or deoxycytidine to the BrdUrd mutagenesis medium (1, 2, 22). The addition of deoxythymidine resulted in less, or even undetectable, BrUra substitution in DNA but the same, or increased, level of mutagenesis (1, 2, 22). Conversely, the addition of deoxycytidine with BrdUrd during mutagenesis resulted in a complete inhibition of mutagenesis but full substitution of BrUra for thymine in DNA (2).These observations have led some investigators to conclude that BrdUrd mutagenesis occurs because of an altered physiological state such as."deoxycytidinelessness" (24) or to implicate BrdUrd metabolites as allosteric effectors of the fidelity of DNA synthetic enzymes (1). It has also been proposed that BrdUrd mutagenesis does not involve mispairing of BrUra during DNA synthesis (5, 10, 22, 25).The conclusion that BrUra base pairs exactly as thymine conflicts with certain experiments termed "clean growth" (23) in which BrUra-substituted DNA was proved to induce replication errors in the absence of exogeno...

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The Stereochemical Basis of Template Function

Cited by 36 publications

References 23 publications

A new approach to the synthesis of a protected 2-aminopurine derivative and its incorporation into oligodeoxynucleotides containing the Eco RI and Bam HI recognition sites

A new approach to the synthesis of a protected 2-aminopurine derivative and its incorporation into oligodeoxynucleotides containing the Eco RI and Bam HI recognition sites

Quantitative measurements on the duplex stability of 2,6‐diaminopurine and 5‐chloro‐uracil nucleotides using enzymatically synthesized oligomers

Deoxyribonucleotide pools, base pairing, and sequence configuration affecting bromodeoxyuridine- and 2-aminopurine-induced mutagenesis.

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