Crystal and Molecular Structure of Adenosine 3′,5′-Cyclic Phosphate

Watenpaugh, Keith David; Dow, Jean; Jensen, L. H.; Furberg, Sven

doi:10.1126/science.159.3811.206

Cited by 114 publications

(39 citation statements)

References 4 publications

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“…Molecules of a mixture of thymidine and dihydrothymidine or a mixture of diastereoisomers of dihydrothymidine may be nearly superimposed except for the atoms corresponding to C(5), C(6) and 0(2). Similar crystallographic evidence for dihydrothymine (Furberg & Jensen, 1968) has been interpreted in terms of a mixture of D and L isomers.…”

Section: Phase Determination and Refinementmentioning

confidence: 75%

The structure of dihydrothymidine

Konnert¹,

Karle²,

Karle³

1970

Acta Crystallogr Sect B

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Dihydrothymidine formed by the catalytic reduction of thymidine exists as only a single diastereoisomer. The six-membered ring in the dihydrothymine moiety has the half-chair conformation and the CHa group on C(5) is equatorial to the ring. In the furanose ring the four carbon atoms are coplanar while the O(1') atom is displaced by 0.42/~ from this plane. The 0(5 )H group in the sugar moiety is disordered with a 2:1 distribution. The material crystallizes in space group P212121 with a=9-554+0.001, b= 21-992 + 0"002, c = 5"475 + 0"001/~ and Z= 4. The structure was determined by application of the symbolic addition procedure for phase determination. The final R value was 5-1%.

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Section: Phase Determination and Refinementmentioning

confidence: 75%

The structure of dihydrothymidine

Konnert¹,

Karle²,

Karle³

1970

Acta Crystallogr Sect B

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“…Backgrounds were measured both at the beginning and end of each scan for lOsec. Three standard reflexions (060, (2) 217( 7) 1529 (3) 393 (10) 1666 (2) 704( 8) 1672 (3) 1436(11) 2031 (2) 1043( 7) 1772 (4) (13) 2835 (17) 3046 (26) 2917 (17) 2581 (18) 2474 (18) 2595 (20) 2500 (17) 2153 (15) 2093 (17) 2390 (14) 2337 (21) 4237 (13) 991 (17) 167 (12) 2420 (20) 1627 (15) 4159 (21) 6059 (25) 6606 (18) 287 (20) 325 (17) 168 (16) 186 (22) 1 (16) 271 (24) 169 (24) 409 (20) 605 (17) 698 (31) 768 (22) 8250 (21) 1372 (18) 890 (19) 678 (18) 230 (21) 45 (20) …”

Section: Nucleic Acids Researchmentioning

confidence: 99%

The crystal and molecular structure of 2′:-deoxy-2′:-fluoroinosine monohydrate

Hakoshima¹,

Omori²,

Tomita³

et al. 1981

Nucl Acids Res

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The structure of the hydrate of 2'-deoxy-2'-fluoroinosine has been determined by single-crystal x-ray diffraction. The nucleoside crystallizes in space group P2 12 121 with unit cell dimensions, a = 33.291, b = 10. 871, c = 6.897A. There are two nucleosides and two water molecules in the asymmetric unit. The structure was solved by direct methods and refined to a residual R = 0.095. The two independent nucleosides in the asymmetric unit show different conformations about the glycosidic bond, while other structural details are similar.

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“…Similar considerations for the rotation about the glycosidic bond indicate that numerous close contacts, for example, C(12) (methyl THE STRUCTURE OF 2-ETHYLTHIO-8-METHYLINOSINE MONOHYDRATE carbon)...C(2'), C(12)...O(2'), H(C12) (hydrogen atom in methyl group)...C(2'), H(C12)...O(l') and H(C12).-~: 0(2') etc., occur in the anti range because of the presence of the 8-methyl group. Cyclic 3',5'-adenosine phosphate (Watenpaugh, Dow, Jensen & Furberg, 1968), inosine and guanosine (Thewalt, Bugg & Marsh, 1970), in which both syn and anti conformations exist in the same crystal, show, as Haschemeyer & Rich (1967) have concluded, that the barriers to the rotation about the glycosidic bond are not high and the base-sugar conformation (~cN) depends on its environment and the crystal packing. In the present compound, the close steric contacts introduced by the methyl group at the 8-position may be responsible for the syn conformation.…”

Section: The Molecular Structurementioning

confidence: 99%

“…(g) Koyama, Maeda, Umezawa & Iitaka (1966). (h) Watenpaugh, Dow, Jensen & Furberg (1968). (i) Thewalt, Bugg & Marsh (1970).…”

Section: The Molecular Structurementioning

confidence: 99%

The crystal and molecular structure of 2-ethylthio-8-methylinosine monohydrate

Nagashima¹,

Wakabayashi²

1974

Acta Crystallogr Sect B

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2-Ethylthio-8-methylinosine monohydrate crystallizes in the space group P21 with unit-cell dimensions: a=10.81, b=6.93, c=10.58 A, /?=96.1 °. The structure was determined by Patterson and Fourier syntheses, and refined by block-diagonal least-squares calculations. The molecule was found to exist in the syn conformation. The sugar ring exhibits a C(2")-endo puckering, and the conformation about the C(4')-C(5') bond is gauche-trans. The purine rings are nearly normal to the b axis and are stacked along the twofold screw axis by overlapping of the planes, each of which involves the ring and the S atom. There are two kinds of intermolecular hydrogen bond between the symmetry-related molecules; one connects N(1)-H of the base to 0(2') of the ribose, and the other connects 0(6) of the base to O(5')-H of the ribose. N(7) of the base is hydrogen bonded to the water molecule which is fixed in its position by three hydrogen bonds.

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Crystal and Molecular Structure of Adenosine 3′,5′-Cyclic Phosphate

Cited by 114 publications

References 4 publications

The structure of dihydrothymidine

The structure of dihydrothymidine

The crystal and molecular structure of 2′:-deoxy-2′:-fluoroinosine monohydrate

The crystal and molecular structure of 2-ethylthio-8-methylinosine monohydrate

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