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Volumn 59, Issue 34, 2003, Pages 6465-6471

A facile synthesis of cyclic bis(3′→5′)diguanylic acid

Author keywords

Cyclisation; Nucleotides; Phosphoramidites

Indexed keywords

CYCLIC BIS(3',5')DIGUANYLIC ACID; GUANOSINE PHOSPHATE; GUANYLYL(3',5')GUANOSINE 3' PHOSPHATE; N 2 (ALLYLOXYCARBONYL) O 6 (ALLYL) 2' O (TERT BUTYLDIMETHYLSILYL)GUANOSINE 3' (ALLYL 2 CYANOETHYL)PHOSPHATE; UNCLASSIFIED DRUG;

EID: 0042703514     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)01045-7     Document Type: Article
Times cited : (45)

References (26)
  • 4
    • 85031132710 scopus 로고    scopus 로고
    • In Refs. 1,2, there is no information about the yield of the desired compound in the deprotection of the N-diphenylacetyl protectors. Thus, we cannot know whether the deprotection causes decomposition of the desired product in the existing synthesis. However, according to experiments carried out by us, cGpGp was decomposed to no small extent by treatment with hot conc. aqueous ammonia to give undesired products. The structure of the products was not determined because analytical samples of them were not obtained though chromatographic purification was attempted under several conditions; we supposed that the products are those resulting from cleavage of internucleotide linkage
    • In Refs. 1,2, there is no information about the yield of the desired compound in the deprotection of the N-diphenylacetyl protectors. Thus, we cannot know whether the deprotection causes decomposition of the desired product in the existing synthesis. However, according to experiments carried out by us, cGpGp was decomposed to no small extent by treatment with hot conc. aqueous ammonia to give undesired products. The structure of the products was not determined because analytical samples of them were not obtained though chromatographic purification was attempted under several conditions; we supposed that the products are those resulting from cleavage of internucleotide linkage.
  • 5
    • 85031130545 scopus 로고    scopus 로고
    • This paper eliminates another defect of the existing synthesis. In the field of chemical synthesis, detailed experimental protocol is very important for reexamination of the synthesis. However, Refs. 1,2 do not describe in detail the protocol; this is troublesome for further investigations. By contrast, this paper provides detailed experimental procedures for all reactions
    • This paper eliminates another defect of the existing synthesis. In the field of chemical synthesis, detailed experimental protocol is very important for reexamination of the synthesis. However, Refs. 1,2 do not describe in detail the protocol; this is troublesome for further investigations. By contrast, this paper provides detailed experimental procedures for all reactions.
  • 11
    • 85031143515 scopus 로고    scopus 로고
    • note
    • 4a and 4b carried out in a similar manner also provided 5 as a sole product. This result also supported the assigned structure of 4a and 4b Deprotection of the single material of 4a and 4b carried out in a similar manner also provided 5 as a sole product. This result also supported the assigned structure of 4a and 4b.
  • 18
    • 85031130718 scopus 로고    scopus 로고
    • 1H NMR spectrum listed in Ref. 1 was taken at 50°C. Therefore, this work also took the spectrum under the same conditions in order to carry out exact comparison of both spectra
    • 1H NMR spectrum listed in Ref. 1 was taken at 50°C. Therefore, this work also took the spectrum under the same conditions in order to carry out exact comparison of both spectra.
  • 19
    • 0028246706 scopus 로고
    • Representative works: (a) Hayakawa Y., Hirose M., Noyori R. Nucleosides Nucleotides. 13:1994;1337-1345 (b) Iyer R.P., Guo M.-J., Yu D., Agrawal S. Tetrahedron Lett. 39:1998;2491-2494 (c) Boesen T., Kehler J., Dahl O. Nucleosides Nucleotides. 18:1999;1241-1242.
    • (1994) Nucleosides Nucleotides , vol.13 , pp. 1337-1345
    • Hayakawa, Y.1    Hirose, M.2    Noyori, R.3
  • 20
    • 0032559980 scopus 로고    scopus 로고
    • Representative works: (a) Hayakawa Y., Hirose M., Noyori R. Nucleosides Nucleotides. 13:1994;1337-1345 (b) Iyer R.P., Guo M.-J., Yu D., Agrawal S. Tetrahedron Lett. 39:1998;2491-2494 (c) Boesen T., Kehler J., Dahl O. Nucleosides Nucleotides. 18:1999;1241-1242.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2491-2494
    • Iyer, R.P.1    Guo, M.-J.2    Yu, D.3    Agrawal, S.4
  • 21
    • 0032811604 scopus 로고    scopus 로고
    • Representative works: (a)
    • Representative works: (a) Hayakawa Y., Hirose M., Noyori R. Nucleosides Nucleotides. 13:1994;1337-1345 (b) Iyer R.P., Guo M.-J., Yu D., Agrawal S. Tetrahedron Lett. 39:1998;2491-2494 (c) Boesen T., Kehler J., Dahl O. Nucleosides Nucleotides. 18:1999;1241-1242.
    • (1999) Nucleosides Nucleotides , vol.18 , pp. 1241-1242
    • Boesen, T.1    Kehler, J.2    Dahl, O.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.