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Volumn 132, Issue 46, 2010, Pages 16677-16688

Erratum: Chemoselective multicomponent one-pot assembly of purine precursors in water (Journal of the American Chemical Society (2010) 132 (16677-16688) DOI:10.1021/ja108197s);Chemoselective multicomponent one-pot assembly of purine precursors in water

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; RNA;

EID: 78649927354     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2002023     Document Type: Erratum
Times cited : (139)

References (71)
  • 2
    • 0003604405 scopus 로고    scopus 로고
    • 2nd ed.; Cold Spring Harbor Laboratory Press: Plainview, NY.
    • Gesteland, R. F., Cech, T. R., and Atkins, J. F., Eds. The RNA World, 2nd ed.; Cold Spring Harbor Laboratory Press: Plainview, NY, 1999.
    • (1999) The RNA World
    • Gesteland, R.F.1    Cech, T.R.2    Atkins, J.F.3
  • 31
    • 78649980677 scopus 로고    scopus 로고
    • Intramolecular trapping of iminium ion 9 can presumably occur reversibly, but it is thought that 6- exo-trig reaction dominates for thermodynamic reasons. See ref 1.
    • Intramolecular trapping of iminium ion 9 can presumably occur reversibly, but it is thought that 6- exo-trig reaction dominates for thermodynamic reasons. See ref 1.
  • 36
    • 78649964950 scopus 로고    scopus 로고
    • note
    • 15N HMBC spectra were used to assign the connectivity of the imidazole nitrogens with respect to H-(C1′). Diastereoisomers were differentiated by a combination of crystallography and 2D NOESY spectroscopy.
  • 38
    • 78649943971 scopus 로고    scopus 로고
    • Equilibration resulting in a 1:4 mixture of 28: 32 is observed over 3 d at 60°C.
    • Equilibration resulting in a 1:4 mixture of 28: 32 is observed over 3 d at 60°C.
  • 39
    • 78649952670 scopus 로고    scopus 로고
    • 13C HMBC analysis of the products of the reaction of glyceraldehyde, 2, and 5 (see Supporting Information, Figure S28).
    • 13C HMBC analysis of the products of the reaction of glyceraldehyde, 2, and 5 (see Supporting Information, Figure S28).
  • 42
    • 33749026850 scopus 로고
    • Though it is possible that the reaction of formaldehyde and 5 is reversible, 41 was not observed to undergo retro-aldol decomposition during synthesis from glyceraldehyde and 4 or upon heating in aqueous solution. Furthermore, it should be noted that neither intramolecular cyclization nor aromatization is required for product trapping to prevent retro-aldol reaction. The reversible interchange of pentose aminooxazolines and their respective oxazoles with open-chain hydrates has been observed in the absence of retro-aldol reaction (see ref 11b). The reaction of 4-methoxybenzaldehyde and 2-amino-4-methyloxazole has been reported (albeit in hot toluene) wherein, due to the lack of a suitably positioned nucleophilic moiety, cyclization to an aminooxazoline cannot occur (ref 19a)
    • Though it is possible that the reaction of formaldehyde and 5 is reversible, 41 was not observed to undergo retro-aldol decomposition during synthesis from glyceraldehyde and 4 or upon heating in aqueous solution. Furthermore, it should be noted that neither intramolecular cyclization nor aromatization is required for product trapping to prevent retro-aldol reaction. The reversible interchange of pentose aminooxazolines and their respective oxazoles with open-chain hydrates has been observed in the absence of retro-aldol reaction (see ref 11b). The reaction of 4-methoxybenzaldehyde and 2-amino-4-methyloxazole has been reported (albeit in hot toluene) wherein, due to the lack of a suitably positioned nucleophilic moiety, cyclization to an aminooxazoline cannot occur (ref 19a). Finally, in aqueous solution, the reaction of glyceraldehyde-2-phosphate and 5 furnishes a diastereomeric mixture of open-chain hydrates. Despite the potential for 6- exo-trig hydroxyl cyclization to afford pyranosyl-aminooxazoline products, heating these hydrate species leads to aromatization not cyclization or retro-aldol decomposition. Khan, H. R. and Crank, G. Tetrahedron Lett. 1987, 28, 3381
    • (1987) Tetrahedron Lett. , vol.28 , pp. 3381
    • Khan, H.R.1    Crank, G.2
  • 57
    • 78649935108 scopus 로고    scopus 로고
    • C2′ stereochemical inversions have been observed in related molecules under both thermal and photochemical condition; see refs 1, 11b, and 22.
    • C2′ stereochemical inversions have been observed in related molecules under both thermal and photochemical condition; see refs 1, 11b, and 22.
  • 58
    • 78649950500 scopus 로고    scopus 로고
    • Proposed six-member imidazole cyclization to furnish 49
    • Proposed six-member imidazole cyclization to furnish 49
  • 61
  • 71
    • 78649912861 scopus 로고    scopus 로고
    • Alternatively, the pH-dependent profiles of the multicomponent reaction described provide a route to 36 - 39 in the presence of 2 and 3. Therefore, subsequent incorporation of the purine fragment with 36, 38, or 39 (or derivatives thereof) still remains a plausible route to purine molecules under prebiotic constraints for their concurrent synthesis with pyrimidine nucleotides accessed via 37.
    • Alternatively, the pH-dependent profiles of the multicomponent reaction described provide a route to 36 - 39 in the presence of 2 and 3. Therefore, subsequent incorporation of the purine fragment with 36, 38, or 39 (or derivatives thereof) still remains a plausible route to purine molecules under prebiotic constraints for their concurrent synthesis with pyrimidine nucleotides accessed via 37.


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