Cyclo­(-l-prolyl-l-valinyl-) from Burkholderia thailandensis MSMB43

Liu, X.-Y.; Wang, C.; Cheng, Y.-Q.

doi:10.1107/S1600536812043000

Volume 68
Part 11
Pages o3182-o3183
November 2012

Received 8 October 2012
Accepted 15 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R = 0.031
wR = 0.075
Data-to-parameter ratio = 13.5
Details

Cyclo(-L-prolyl-L-valinyl-) from Burkholderia thailandensis MSMB43

Xiang-Yang Liu,^a Cheng Wang ^a ^* and Yi-Qiang Cheng ^a ^*

^aDepartment of Biological Sciences, Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, PO Box 413, Milwaukee, WI 53201, USA
Correspondence e-mail: wang35@uwm.edu, ycheng@uwm.edu

The title compound [systematic name: (3S,8aS)-3-isopropylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione], C₁₀H₁₆N₂O₂,, is a newly isolated cyclic dipeptide from Burkholderia thailandensis MSMB43. There are two independent molecules in the asymmetric unit. Two C atoms and their attached H atoms in the five-membered ring of one of the molecules are disordered over two sets of sites in a 0.715 (5):0.285 (5) ratio. The two independent molecules have the same configuration and the absolute configurations of the chiral centers were determined based on the observation of anomalous dispersion. In the crystal, two types of N-HO hydrogen bonds link pairs of independent molecules.

Related literature

For general background to secondary metabolites from B. thailandensis, see: Knappe et al. (2008); Nguyen et al. (2008); Seyedsayamdost et al. (2010); Ishida et al. (2010); Klausmeyer et al. (2011); Biggins et al. (2011); Wang et al. (2011, 2012); Ishida et al. (2012). For isolation of the title compound from other microorganisms, see: Chen (1960); Schmitz et al. (1983); Jayatilake et al. (1996); Ginz & Engelhardt (2000); Qi et al. (2009); Wang et al. (2010); Park et al. (2006). For the biological activity of the title compound, see: Holden et al. (1999); Fdhila et al. (2003). For large-scale genome sequencing, see: Mukhopadhyay et al. (2010); Yu et al. (2006); Zhuo et al. (2012). For our work on obtaining natural products from B. thailandensis MSMB43, see: Liu et al. (2012).

Experimental

Crystal data

C₁₀H₁₆N₂O₂
M_r = 196.25
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.6227 (1) Å
b = 10.2571 (2) Å
c = 34.2115 (6) Å
V = 1973.07 (6) Å³
Z = 8
Cu K radiation
= 0.76 mm^-1
T = 100 K
0.22 × 0.14 × 0.10 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007) T_min = 0.851, T_max = 0.928
28285 measured reflections
3668 independent reflections
3354 reflections with I > 2(I)
R_int = 0.045

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.075
S = 1.02
3668 reflections
271 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.30 e Å^-3
_min = -0.23 e Å^-3
Absolute structure: Flack (1983), 1481 Friedel pairs
Flack parameter: 0.05 (17)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1Aⁱ	0.872 (19)	2.016 (19)	2.8734 (17)	167.7 (17)
N1A-H1AO1ⁱⁱ	0.916 (19)	2.06 (2)	2.9710 (17)	172.3 (17)
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXTL and OLEX2.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2084 ).

Acknowledgements

Support for this work was obtained from a Research Growth Initiative Award from the University of Wisconsin-Milwaukee and NIH/NCI grant R01 CA 152212 (both to YQC). The authors thank Lara C. Spencer and Ilia A. Guzei (University of Wisconsin-Madison Department of Chemistry Crystallography Facility) for collecting the crystallographic data.

References

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organic compounds