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. 1973 Jan;70(1):279–283. doi: 10.1073/pnas.70.1.279

The Crystal Structures of 2,5-Piperazinediones Having Epipolysulfide Bridges Between C3 and C6: The Structures of N,N′-Dimethyl-3,6-Epitetrathio-2,5-Piperazinedione

Betty R Davis 1, Ivan Bernal 1,*
PMCID: PMC433231  PMID: 16592049

Abstract

The crystal and molecular structure of N,N′-dimethyl-3,6-epitetrathio-2,5-piperazinedione (C6H8O2N2S4) has been determined from three-dimensional x-ray diffraction data collected by counter techniques. The substance crystallizes in the orthorhombic space group Fdd2, with a = 15.352(5), b = 20.432(7), and c = 6.635(2) Å; V = 2081.2(8) Å3, D(meas) = 1.72(2) g/cm3, and z = 8 molecules per unit cell. The molecule lies on a crystallographic 2-fold axis, the piperazinedione ring is in the boat conformation, and the deviation from planarity is 18°. The bonds of the tetrasulfide chain alternate in length so that the S-S distances are 2.0244(9), 2.076(1), and 2.0244(9) Å. The structural data were refined by least-squares methods to an R(F) of 2.5% by use of the 1089 independent reflections (2θ ≤ 71°; MoKα) for which F02 ≥ 3σ (F02). Since this molecule is chemically identical with the active center of the recently isolated natural product sporidesmin G, our structural study constitutes a description of the epitetrathio-2,5-piperazinedione fragment of that molecule.

Keywords: x-ray structures, cyclic dipeptides, active site of sporidesmin G, viral inhibitors, cytotoxins, Pythomyces chartarum

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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