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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 [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.031
wR = 0.075
Data-to-parameter ratio = 13.5
Details
Open access

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

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-H...O hydrogen bonds link pairs of independent molecules.

Related literature

For general background to secondary metabolites from B. thailandensis, see: Knappe et al. (2008[Knappe, T. A., Linne, U., Zirah, S., Rebuffat, S., Xie, X. & Marahiel, M. A. (2008). J. Am. Chem. Soc. 130, 11446-11454.]); Nguyen et al. (2008[Nguyen, T., Ishida, K., Jenke-Kodama, H., Dittmann, E., Gurgui, C., Hochmuth, T., Taudien, S., Platzer, M., Hertweck, C. & Piel, J. (2008). Nat. Biotechnol. 26, 225-233.]); Seyedsayamdost et al. (2010[Seyedsayamdost, M. R., Chandler, J. R., Blodgett, J. A., Lima, P. S., Duerkop, B. A., Oinuma, K., Greenberg, E. P. & Clardy, J. (2010). Org. Lett. 12, 716-719.]); Ishida et al. (2010[Ishida, K., Lincke, T., Behnken, S. & Hertweck, C. (2010). J. Am. Chem. Soc. 132, 13966-13968.]); Klausmeyer et al. (2011[Klausmeyer, P., Shipley, S. M., Zuck, K. M. & McCloud, T. G. (2011). J. Nat. Prod. 74, 2039-2044.]); Biggins et al. (2011[Biggins, J. B., Gleber, C. D. & Brady, S. F. (2011). Org. Lett. 13, 1536-1539.]); Wang et al. (2011[Wang, C., Henkes, L. M., Doughty, L. B., He, M., Wang, D., Meyer-Almes, F. J. & Cheng, Y. Q. (2011). J. Nat. Prod. 74, 2031-2038.], 2012[Wang, C., Flemming, C. J. & Cheng, Y. Q. (2012). MedChemComm, 3, 976-981.]); Ishida et al. (2012[Ishida, K., Lincke, T. & Hertweck, C. (2012). Angew. Chem. Int. Ed. Engl. 51, 5470-5474.]). For isolation of the title compound from other microorganisms, see: Chen (1960[Chen, Y. S. (1960). Bull. Chem. Soc. Jpn, 24, 372-381.]); Schmitz et al. (1983[Schmitz, F. J., Vanderah, D. J., Hollenbeak, K. H., Enwall, C. E. L. & Gopichand, Y. (1983). J. Org. Chem. 48, 3941-3945.]); Jayatilake et al. (1996[Jayatilake, G. S., Thornton, M. P., Leonard, A. C., Grimwade, J. E. & Baker, B. J. (1996). J. Nat. Prod. 59, 293-296.]); Ginz & Engelhardt (2000[Ginz, M. & Engelhardt, U. H. (2000). J. Agric. Food Chem. 48, 3528-3532.]); Qi et al. (2009[Qi, S. H., Xu, Y., Gao, J., Qian, P. Y. & Zhang, S. (2009). Anna. Microbiol. 59, 229-233.]); Wang et al. (2010[Wang, J. H., Quan, C. S., Qi, X. H., Li, X. & Fan, S. D. (2010). Ann. Microbiol. 396, 1773-1779.]); Park et al. (2006[Park, Y. C., Gunasekera, S. P., Lopez, J. V., McCarthy, P. J. & Wright, A. E. (2006). J. Nat. Prod. 69, 580-584.]). For the biological activity of the title compound, see: Holden et al. (1999[Holden, M. T., Ram Chhabra, S., de Nys, R., Stead, P., Bainton, N. J., Hill, P. J., Manefield, M., Kumar, N., Labatte, M., England, D., Rice, S., Givskov, M., Salmond, G. P., Stewart, G. S., Bycroft, B. W., Kjelleberg, S. & Williams, P. (1999). Mol. Microbiol. 33, 1254-1266.]); Fdhila et al. (2003[Fdhila, F., Vazquez, V., Sanchez, J. L. & Riguera, R. (2003). J. Nat. Prod. 66, 1299-1301.]). For large-scale genome sequencing, see: Mukhopadhyay et al. (2010[Mukhopadhyay, S., Thomason, M. K., Lentz, S., Nolan, N., Willner, K., Gee, J. E., Glass, M. B., Inglis, T. J., Merritt, A., Levy, A., Sozhamannan, S., Mateczun, A. & Read, T. D. (2010). J. Bacteriol. 192, 6313-6314.]); Yu et al. (2006[Yu, Y., Kim, H. S., Chua, H. H., Lin, C. H., Sim, S. H., Lin, D., Derr, A., Engels, R., DeShazer, D., Birren, B., Nierman, W. C. & Tan, P. (2006). BMC Microbiol. 6, 46.]); Zhuo et al. (2012[Zhuo, Y., Liu, L., Wang, Q., Liu, X., Ren, B., Liu, M., Ni, P., Cheng, Y. Q. & Zhang, L. (2012). J. Bacteriol. 194, 4749-4750.]). For our work on obtaining natural products from B. thailandensis MSMB43, see: Liu et al. (2012[Liu, X.-Y., Wang, C. & Cheng, Y.-Q. (2012). Acta Cryst. E68, o2757-o2758.]).

[Scheme 1]

Experimental

Crystal data
  • C10H16N2O2

  • Mr = 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[alpha] radiation

  • [mu] = 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[Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.851, Tmax = 0.928

  • 28285 measured reflections

  • 3668 independent reflections

  • 3354 reflections with I > 2[sigma](I)

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1481 Friedel pairs

  • Flack parameter: 0.05 (17)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1Ai 0.872 (19) 2.016 (19) 2.8734 (17) 167.7 (17)
N1A-H1A...O1ii 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[Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); 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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Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, Y. S. (1960). Bull. Chem. Soc. Jpn, 24, 372-381.  [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Fdhila, F., Vazquez, V., Sanchez, J. L. & Riguera, R. (2003). J. Nat. Prod. 66, 1299-1301.  [ISI] [CrossRef] [PubMed] [ChemPort]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Ginz, M. & Engelhardt, U. H. (2000). J. Agric. Food Chem. 48, 3528-3532.  [ISI] [CrossRef] [PubMed] [ChemPort]
Holden, M. T., Ram Chhabra, S., de Nys, R., Stead, P., Bainton, N. J., Hill, P. J., Manefield, M., Kumar, N., Labatte, M., England, D., Rice, S., Givskov, M., Salmond, G. P., Stewart, G. S., Bycroft, B. W., Kjelleberg, S. & Williams, P. (1999). Mol. Microbiol. 33, 1254-1266.  [CrossRef] [PubMed] [ChemPort]
Ishida, K., Lincke, T., Behnken, S. & Hertweck, C. (2010). J. Am. Chem. Soc. 132, 13966-13968.  [ISI] [CrossRef] [ChemPort] [PubMed]
Ishida, K., Lincke, T. & Hertweck, C. (2012). Angew. Chem. Int. Ed. Engl. 51, 5470-5474.  [ISI] [CrossRef] [ChemPort] [PubMed]
Jayatilake, G. S., Thornton, M. P., Leonard, A. C., Grimwade, J. E. & Baker, B. J. (1996). J. Nat. Prod. 59, 293-296.  [CrossRef] [ChemPort] [PubMed] [ISI]
Klausmeyer, P., Shipley, S. M., Zuck, K. M. & McCloud, T. G. (2011). J. Nat. Prod. 74, 2039-2044.  [ISI] [CrossRef] [ChemPort] [PubMed]
Knappe, T. A., Linne, U., Zirah, S., Rebuffat, S., Xie, X. & Marahiel, M. A. (2008). J. Am. Chem. Soc. 130, 11446-11454.  [ISI] [CrossRef] [PubMed] [ChemPort]
Liu, X.-Y., Wang, C. & Cheng, Y.-Q. (2012). Acta Cryst. E68, o2757-o2758.  [CSD] [CrossRef] [details]
Mukhopadhyay, S., Thomason, M. K., Lentz, S., Nolan, N., Willner, K., Gee, J. E., Glass, M. B., Inglis, T. J., Merritt, A., Levy, A., Sozhamannan, S., Mateczun, A. & Read, T. D. (2010). J. Bacteriol. 192, 6313-6314.  [ISI] [CrossRef] [ChemPort] [PubMed]
Nguyen, T., Ishida, K., Jenke-Kodama, H., Dittmann, E., Gurgui, C., Hochmuth, T., Taudien, S., Platzer, M., Hertweck, C. & Piel, J. (2008). Nat. Biotechnol. 26, 225-233.  [ISI] [CrossRef] [PubMed] [ChemPort]
Park, Y. C., Gunasekera, S. P., Lopez, J. V., McCarthy, P. J. & Wright, A. E. (2006). J. Nat. Prod. 69, 580-584.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Qi, S. H., Xu, Y., Gao, J., Qian, P. Y. & Zhang, S. (2009). Anna. Microbiol. 59, 229-233.  [CrossRef] [ChemPort]
Schmitz, F. J., Vanderah, D. J., Hollenbeak, K. H., Enwall, C. E. L. & Gopichand, Y. (1983). J. Org. Chem. 48, 3941-3945.
Seyedsayamdost, M. R., Chandler, J. R., Blodgett, J. A., Lima, P. S., Duerkop, B. A., Oinuma, K., Greenberg, E. P. & Clardy, J. (2010). Org. Lett. 12, 716-719.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, C., Flemming, C. J. & Cheng, Y. Q. (2012). MedChemComm, 3, 976-981.  [CrossRef] [ChemPort]
Wang, C., Henkes, L. M., Doughty, L. B., He, M., Wang, D., Meyer-Almes, F. J. & Cheng, Y. Q. (2011). J. Nat. Prod. 74, 2031-2038.  [ISI] [CrossRef] [ChemPort] [PubMed]
Wang, J. H., Quan, C. S., Qi, X. H., Li, X. & Fan, S. D. (2010). Ann. Microbiol. 396, 1773-1779.  [ChemPort]
Yu, Y., Kim, H. S., Chua, H. H., Lin, C. H., Sim, S. H., Lin, D., Derr, A., Engels, R., DeShazer, D., Birren, B., Nierman, W. C. & Tan, P. (2006). BMC Microbiol. 6, 46.
Zhuo, Y., Liu, L., Wang, Q., Liu, X., Ren, B., Liu, M., Ni, P., Cheng, Y. Q. & Zhang, L. (2012). J. Bacteriol. 194, 4749-4750.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2012). E68, o3182-o3183   [ doi:10.1107/S1600536812043000 ]

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