The crystal structure of deoxyadenosine monohydrate

Watson, D. G.; Sutor, D. June; Tollin, P.

doi:10.1107/s0365110x65002852

Cited by 126 publications

(41 citation statements)

References 9 publications

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“…The bond length of 1.467 (10)A for C(2)-C (3) appears shorter than the average C-C single bond distance of 1.506 A in succinimide (Mason, 1961) and the average C-C single bond distance of 1.49 A in succinic anhydride (Ehrenberg, 1965); also it is even shorter than the average C-C bond lengths (1.515 A) of the five-membered ring in deoxyadenosine monohydrate (Watson, Sutor & Tollin, 1965) and of 1.524 ]k in adenosine 3'-phosphate dihydrate (Sundaralingam, 1966). The shortening of this bond length indicates that in addition to the conjugative effect in the fivemembered ring and the resonance effect in the C=O double bond, the unsaturated character of the cyclopropane ring contributes an unusual effect in bond shortening.…”

Section: Discussionmentioning

confidence: 99%

The crystal and molecular structure of 12-methyl-11,13-dioxo-12-azapentacyclo[4,4,3,01.6,02.10,05.7]trideca-3,8-diene

Hwang¹,

Donohue²,

Tsai³

1972

Acta Crystallogr Sect B

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Crystals of the title compound, CaaHxxO2N, are orthorhombic, space group Fdd2, Z= 8, a=27.289 + 0.004, b = 13.108 + 0.005, c = 9-165 + 0.002/~, Dx = 1.362 g.cm -3. Data for 454 reflections were collected at room temperature on a Picker automated diffractometer. The structure was solved by direct methods, using a computerized multiple-solution procedure, and it was refined by full-matrix least-squares methods to a final R on F of 0"046, with 377 observed reflections. The average e.s.d.'s of the bond lengths and angles not involving hydrogen are about 0.008 A and 0.5 °, respectively. Bond lengths and angles were corrected for thermal motion. Some C-C single bonds are found to be significantly shorter than the normal C-C single bond length of 1.54 A. The shortening of the C-C bonds is explained by the conjugation of the C=O bond and C=C bond with the three-membered ring.

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Section: Discussionmentioning

confidence: 99%

The crystal and molecular structure of 12-methyl-11,13-dioxo-12-azapentacyclo[4,4,3,01.6,02.10,05.7]trideca-3,8-diene

Hwang¹,

Donohue²,

Tsai³

1972

Acta Crystallogr Sect B

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“…2'-dA: 2'-deoxyadenosine (Watson, Sutor & Tollin, 1965); A: adenosine (Lai & Marsh, 1972); araA: adenine arabinofuranoside (Chwang & Sundaralingam, 1974);3'-dA: 3'-deoxyadenosine (present study). adenosine is the rather unusual C(3')-exo pucker (Table 5).…”

Section: C(y)-exo C(y)-endo C(3')-endo C(3')-endomentioning

confidence: 58%

The structure of cordycepin

Radwan¹,

Wilson²

1980

Acta Crystallogr Sect B

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“…2, are formed between molecules related by the 21 screw along a; these base pairs are formed by N(6)--H.-.N(7') and N(6')-H...N(1) hydrogen bonds of length 2.891 (4) and 2.931 (4) A, respectively,-with associated N-H...N angles of 162 and 154 ° respectively. This base-pairing configuration, which is reminiscent of both the Watson-Crick and Hoogsteen models for adeninethymine base pairs, has been observed in several other neutral adenine derivatives including 9-methyladenine (Stewart & Jensen, 1964), deoxyadenosine (Watson, Sutor & Tollin, 1965), and 2'-O-methyladenosine ( Prusiner & Sundaralingam, 1976). The N(6')-H...N(1) separation in the present complex is within the range of 2.88 to 3.00 A observed in these other structures, but the N(6)-H...N(7') distance of 2.891 (4) A is significantly shorter than those of 3.00 to 3.06/k previously observed.…”

mentioning

confidence: 64%