Mechanism for the conversion of right‐handed DNA helices into the left‐handed isomers. Part II

Marianne M . C. F. Castelijns et al. 1 Salt-induced conversioti.v 1 4 /'( V ) i i i i o P( I V ) in solvents of different polarity Full papers Salt-induced conversions of P(V) into P(IV) in solvents of different polarity.Abstract. Evidence is presented for the involvement of pentaco-ordinated phosphorus intermediates in the rate-determining step of the de-alkylation reactions of some phosphates and phosphonates with LiCl and LiBr. Such involvement is suggested to lead to the zwitterionic pentaco-ordinated phosphorus complexes 5a and 5b, respectively when compounds 2a and 2b are treated with LiCl and LiBr. The existence of these complexes shows unambiguously the possibility of inducing (slight) conformational changes of phosphorus in the presence of cations and anions (or nucleophilic solvents). This approach may also be useful for the description of conformational changes in phosphate residues in DNA, thus leading to different conformations of DNA. Salt-induced conversions of P ( V ) into P ( I V ) in solventsof difSerent polarity: intramolecular group transfer. Nature 247, 558 (1974). l4 H . M. Buck, Red. Trav. Chim. Pays-Bas 99, 181 (1980).

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Salt‐induced conversions of P(V) into P(IV) in solvents of different polarity. A tentative model for the initiation of conformational changes in DNA via the P(IV) residues

Castelijns

Aken

Schipper

et al. 1980

Recl. Trav. Chim. Pays‐Bas

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Mechanistic aspects of organophosphorus chemistry

Buck

1981

Recl. Trav. Chim. Pays‐Bas

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Dynamics of DNA. A quantumchemical study

VanLier

Koole

Buck

1983

Recl. Trav. Chim. Pays‐Bas

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Johan J . C. van Lier et al. /Dynamics of DNA. A quantumchemical study Recl. Trav. Chim. Pays-BasAbstract. On the basis of CNDO-2 and MNDO quantumchemical calculations we suggest that direct generation of Pv trigonal bipyramidal (TBP) intermediates, in pC and pT fragments of ds DNA with repetitive purine-pyrimidine sequences, results in the B + Z transition via a selective pathway. The calculations reveal that 5'-d(G,C), 5'-d(G,T), 5'-d(A,C) and 5'-d(A,T) fragments are selected to initiate the B + Z transition. We therefore suggest that the cooperative B + Z transition can only proceed in helices having repetitive GC, GT, AC or AT sequences.Abstract. Two epimeric steroidal allenes, 1 and 2, have been interconverted by reaction with Me,CuMgCI and Me,CuLi. MeCu could also be used, although in this case the isomerisation was much slower. The 1,4-disubstituted butatrienes 6 and 8 have also been isomerised by means of Me,CuMgCI and MeCu, while the trisubstituted butatriene 2-7 has been isomerised into its geometric isomer using Et,CuMgCI. The isomerisations are thought to proceed through radical anions. In the case of the butatriene series, it is assumed that the carbometallation of the inner double bond by the copper(1) reagents also proceeds through the proposed radical anion intermediates.

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Mechanism for the conversion of right‐handed DNA helices into the left‐handed isomers. Part II

Cited by 4 publications

References 3 publications

Salt‐induced conversions of P(V) into P(IV) in solvents of different polarity. A tentative model for the initiation of conformational changes in DNA via the P(IV) residues

Salt‐induced conversions of P(V) into P(IV) in solvents of different polarity. A tentative model for the initiation of conformational changes in DNA via the P(IV) residues

Mechanistic aspects of organophosphorus chemistry

Dynamics of DNA. A quantumchemical study

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