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Tetrahedron Letters
Volumn 35, Issue 15, 1994, Pages 2331-2334
4′,6′-Methano carbocyclic thymidine: A conformationally constrained building block for oligonucleotides
Author keywords

[No Author keywords available]
Indexed keywords

4',6' METHANO CARBOCYCLIC THYMIDINE; CARBOCYCLIC THYMIDINE; OLIGONUCLEOTIDE; THYMIDINE DERIVATIVE; UNCLASSIFIED DRUG;
EID: 0028299975     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(94)85212-X     Document Type: Article
Times cited : (154)
References (32)
  • 6
    • 0026537060 scopus 로고
    • The importance of conformational preorganization in nucleic acid hybridization is excellently demonstrated by Eschenmoser's work on homo-DNA:
    • (1992) Helv. Chim. Acta , vol.75 , pp. 218
    • Eschenmoser1    Dobler2
  • 8
    • 84987491049 scopus 로고
    • Nucleic-Acid Analogues with Constraint Conformational Flexibility in the Sugar-Phosphate Backbone (?Bicyclo-DNA?). Part 1. Preparation of (3S,5?R)-2?-Deoxy-3?,5?-ethano-??-D-ribonucleosides (?Bicyclonucleosides?)
    • A different type of constrained oligonucleotide building block incorporating a modified sugar moiety has been reported:
    • (1993) Helvetica Chimica Acta , vol.76 , pp. 481
    • Tarköy1    Bolli2    Schweizer3    Leumann4
  • 15
    • 0027383216 scopus 로고
    • Related ideas have recently been independently applied to the design of bicylo[3.1.0]hexane based 2′,3′-dideoxynucleoside analogs and it was shown that the 3′-deoxy analog of 1 (Fig. 1, Base = thymine) adopts a boat-like conformation in aqueous solution:
    • (1993) Tetrahedron Lett. , vol.34 , pp. 6233
    • Rodriguez1    Marquez2    Nicklaus3    Barchi4
  • 16
    • 84913022419 scopus 로고    scopus 로고
    • The use of bicyclo[3.1.0]hexane based nucleoside analogs as oligonucleotide building blocks was originally suggested to us by Prof. A. Eschenmoser (ETH Zürich) and was first pursued for 1′,6′-methano derivatives (Altmann, K.-H.; Imwinkelried, R.; Eschenmoser, A. Eur. Pat. Appl. EP-A-0 577 558; manuscript in preparation). The results emerging from this study led to the design of compounds of type I.
  • 18
    • 84913035475 scopus 로고    scopus 로고
    • 10a, we have not been able to obtain the cyclopentenone precursor of 2 in enantiomerically pure form.
  • 25
    • 84913025630 scopus 로고    scopus 로고
    • 14 and our own experience with ribo-thymidine.
  • 26
    • 84913038594 scopus 로고    scopus 로고
    • 2O, TMS): δ = 7.55 (s, 1H, H-6); 4.60 (m, 2H, H-1′ + H-3′); 4.00 (d, J=14Hz, 1H, H-5′); 3.15 (d, J=15Hz, 1H, H-5′); 1.85 (m, 2H, H-2′); 1.30 (m, 1H, H-6′); 0.75 (m, 1H, H-7′); 0.60 (m, 1H, H-7′).
  • 27
    • 84913062738 scopus 로고    scopus 로고
    • The structure was solved by direct methods (SDP MULTAN 82). Full matrix least squares refinements with anisotropic temperature factors for all non-H-atoms converged at an R-factor of 0.069. All H-atoms could be located in the difference Fourier map. Inclusion of H-atoms in the least squares refinements improved the R-factor to 0.058.
  • 28
    • 84913080583 scopus 로고    scopus 로고
    • 22 gave the correct masses. It should be noted, however, that the coupling efficiency of 7 was extremely low, which so far has effectively prevented the synthesis of oligonucleotides incorporating two or more bicyclic thymidine residues 1.
  • 32
    • 84913016361 scopus 로고    scopus 로고
    • +, 0.1 mM EDTA, at oligonucleotide concentrations of 4 μM/strand.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.