Intramolecular base-backbone association in 8-bromo-2',3'-O-isopropylidene-adenosine : detection of an O(5')-H...N(3) hydrogen bond via a long range H(5'')-N(3) spin-spin coupling

L.H. Koole; Hans Boer, de; J.W. Haan, de; C.A.G. Haasnoot; P. Dael, van; H.M. Buck

doi:10.1039/c39860000362

Intramolecular base-backbone association in 8-bromo-2',3'-O-isopropylidene-adenosine : detection of an O(5')-H...N(3) hydrogen bond via a long range H(5'')-N(3) spin-spin coupling

L.H. Koole, Hans Boer, de, J.W. Haan, de, C.A.G. Haasnoot, P. Dael, van, H.M. Buck

Chemical Engineering and Chemistry

Research output: Contribution to journal › Article › Academic › peer-review

22 Citations (Scopus)

177 Downloads (Pure)

Abstract

A completely rigid conformation is found for the syn-nucleoside 8-bromo-2,3-O-isopropylidene-adenosine in apolar solvents, which is due to an effective O(5)–H N(3) hydrogen bond, as is demonstrated by a substantial N(3) quadrupolar broadening of the H(5) resonances in the 1H n.m.r. spectra.

Original language	English
Pages (from-to)	362-364
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	4
DOIs	https://doi.org/10.1039/c39860000362
Publication status	Published - 1986

Access to Document

10.1039/c39860000362

619631Final published version, 191 KB

Cite this

Koole, L. H., Boer, de, H., Haan, de, J. W., Haasnoot, C. A. G., Dael, van, P., & Buck, H. M. (1986). Intramolecular base-backbone association in 8-bromo-2',3'-O-isopropylidene-adenosine : detection of an O(5')-H...N(3) hydrogen bond via a long range H(5'')-N(3) spin-spin coupling. Journal of the Chemical Society, Chemical Communications, (4), 362-364. https://doi.org/10.1039/c39860000362

@article{b619a8e1fc324a42a94b10619baabedc,

title = "Intramolecular base-backbone association in 8-bromo-2',3'-O-isopropylidene-adenosine : detection of an O(5')-H...N(3) hydrogen bond via a long range H(5'')-N(3) spin-spin coupling",

abstract = "A completely rigid conformation is found for the syn-nucleoside 8-bromo-2,3-O-isopropylidene-adenosine in apolar solvents, which is due to an effective O(5)–H N(3) hydrogen bond, as is demonstrated by a substantial N(3) quadrupolar broadening of the H(5) resonances in the 1H n.m.r. spectra.",

author = "L.H. Koole and {Boer, de}, Hans and {Haan, de}, J.W. and C.A.G. Haasnoot and {Dael, van}, P. and H.M. Buck",

year = "1986",

doi = "10.1039/c39860000362",

language = "English",

pages = "362--364",

journal = "Journal of the Chemical Society, Chemical Communications",

issn = "0022-4936",

publisher = "Chemical Society",

number = "4",

}

Koole, LH, Boer, de, H, Haan, de, JW, Haasnoot, CAG, Dael, van, P & Buck, HM 1986, 'Intramolecular base-backbone association in 8-bromo-2',3'-O-isopropylidene-adenosine : detection of an O(5')-H...N(3) hydrogen bond via a long range H(5'')-N(3) spin-spin coupling', Journal of the Chemical Society, Chemical Communications, no. 4, pp. 362-364. https://doi.org/10.1039/c39860000362

Intramolecular base-backbone association in 8-bromo-2',3'-O-isopropylidene-adenosine : detection of an O(5')-H...N(3) hydrogen bond via a long range H(5'')-N(3) spin-spin coupling. / Koole, L.H.; Boer, de, Hans; Haan, de, J.W. et al.
In: Journal of the Chemical Society, Chemical Communications, No. 4, 1986, p. 362-364.

Research output: Contribution to journal › Article › Academic › peer-review

TY - JOUR

T1 - Intramolecular base-backbone association in 8-bromo-2',3'-O-isopropylidene-adenosine : detection of an O(5')-H...N(3) hydrogen bond via a long range H(5'')-N(3) spin-spin coupling

AU - Koole, L.H.

AU - Boer, de, Hans

AU - Haan, de, J.W.

AU - Haasnoot, C.A.G.

AU - Dael, van, P.

AU - Buck, H.M.

PY - 1986

Y1 - 1986

N2 - A completely rigid conformation is found for the syn-nucleoside 8-bromo-2,3-O-isopropylidene-adenosine in apolar solvents, which is due to an effective O(5)–H N(3) hydrogen bond, as is demonstrated by a substantial N(3) quadrupolar broadening of the H(5) resonances in the 1H n.m.r. spectra.

AB - A completely rigid conformation is found for the syn-nucleoside 8-bromo-2,3-O-isopropylidene-adenosine in apolar solvents, which is due to an effective O(5)–H N(3) hydrogen bond, as is demonstrated by a substantial N(3) quadrupolar broadening of the H(5) resonances in the 1H n.m.r. spectra.

U2 - 10.1039/c39860000362

DO - 10.1039/c39860000362

M3 - Article

SN - 0022-4936

SP - 362

EP - 364

JO - Journal of the Chemical Society, Chemical Communications

JF - Journal of the Chemical Society, Chemical Communications

IS - 4

ER -

Intramolecular base-backbone association in 8-bromo-2',3'-O-isopropylidene-adenosine : detection of an O(5')-H...N(3) hydrogen bond via a long range H(5'')-N(3) spin-spin coupling

Abstract

Access to Document

Fingerprint

Cite this