Skip to main content Accessibility help
×
Home

Crystal structure of mupirocin form I, C26H44O9

Published online by Cambridge University Press:  08 April 2016

James A. Kaduk
Affiliation:
Illinois Institute of Technology, 3101 S. Dearborn Street, Chicago, Illinois 60616
Kai Zhong
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, Pennsylvania 19073-3273
Amy M. Gindhart
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, Pennsylvania 19073-3273
Thomas N. Blanton
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, Pennsylvania 19073-3273
Corresponding

Abstract

The crystal structure of mupirocin Form I has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional techniques. Mupirocin Form I crystallizes in space group P21 (#4) with a = 12.562 81(16), b = 5.103 63(4), c = 21.713 34(29) Å, β = 100.932(1)°, V = 1366.91(2) Å3, and Z = 2. Although the three hydroxyl groups and the carboxylic acid participate in a three-dimensional hydrogen bond network, the crystal energy appears to be dominated by van der Waals interactions. The Rietveld-refined and density functional optimized structures differ significantly. The powder pattern has been submitted to ICDD for inclusion in the Powder Diffraction File.

Type
Technical Articles
Copyright
Copyright © International Centre for Diffraction Data 2016 

Access options

Get access to the full version of this content by using one of the access options below.

References

Accelrys (2013). Materials Studio 7.0 (Accelrys Software Inc., San Diego, CA).Google Scholar
Allen, F. H. (2002). “The Cambridge Structural Database: a quarter of a million crystal structures and rising,” Acta Crystallogr., B: Struct. Sci. 58, 380388.CrossRefGoogle ScholarPubMed
Altomare, A., Cuocci, C., Giacovazzo, C., Moliterni, A., Rizzi, R., Corriero, N., and Falcicchio, A. (2013). “EXPO2013: a kit of tools for phasing crystal structures from powder data”, J. Appl. Crystallogr. 46, 12311235.CrossRefGoogle Scholar
Bernstein, J., Davis, R. E., Shimoni, L., and Chang, N. L. (1995). “Patterns in hydrogen bonding: functionality and graph set analysis in crystals,” Angew. Chem. Int. Ed. Engl. 34(15), 15551573.CrossRefGoogle Scholar
Bravais, A. (1866). Etudes Cristallographiques (Gauthier Villars, Paris).Google Scholar
Bruno, I. J., Cole, J. C., Kessler, M., Luo, J., Motherwell, W. D. S., Purkis, L. H., Smith, B. R., Taylor, R., Cooper, R. I., Harris, S. E., and Orpen, A. G. (2004). “Retrieval of crystallographically-derived molecular geometry information,” J. Chem. Inf. Sci. 44, 21332144.CrossRefGoogle ScholarPubMed
David, W. I. F., Shankland, K., van de Streek, J., Pidcock, E., Motherwell, W. D. S., and Cole, J. C. (2006). “DASH: a program for crystal structure determination from powder diffraction data,” J. Appl. Crystallogr. 39, 910915.CrossRefGoogle Scholar
Donnay, J. D. H. and Harker, D. (1937). “A new law of crystal morphology extending the law of Bravais,” Am. Mineral. 22, 446467.Google Scholar
Dovesi, R., Orlando, R., Civalleri, B., Roetti, C., Saunders, V. R., and Zicovich-Wilson, C. M. (2005). “CRYSTAL: a computational tool for the ab initio study of the electronic properties of crystals,” Z. Kristallogr. 220, 571573.Google Scholar
Etter, M. C. (1990). “Encoding and decoding hydrogen-bond patterns of organic compounds,” Acc. Chem. Res. 23(4), 120126.CrossRefGoogle Scholar
Finger, L. W., Cox, D. E., and Jephcoat, A. P. (1994). “A correction for powder diffraction peak asymmetry due to axial divergence,” J. Appl. Crystallogr. 27(6), 892900.CrossRefGoogle Scholar
Friedel, G. (1907). “Etudes sur la loi de Bravais,” Bull. Soc. Fr. Mineral. 30, 326455.Google Scholar
Fuller, A. T., Mellows, G., Woolford, M., Banks, G. T., Barrow, K. D., and Chain, E. B. (1971). “Pseudomonic acid: an antibiotic produced by Pseudomonas fluorescens,” Nature 234, 416417.CrossRefGoogle ScholarPubMed
Gatti, C., Saunders, V. R., and Roetti, C. (1994). “Crystal-field effects on the topological properties of the electron-density in molecular crystals - the case of urea,” J. Chem. Phys. 101, 1068610696.CrossRefGoogle Scholar
Greenway, M. J., Salt, S. D., Valder, C. E., and Curzons, A. D. (1997). “Polymorphs of Crystalline Mupirocin,” U.S. Patent 5,594,026.Google Scholar
Hirshfeld, F. L. (1977). “Bonded-atom fragments for describing molecular charge densities,” Theor. Chem. Acta 44, 129138.CrossRefGoogle Scholar
ICDD (2014), PDF-4+ 2014 (Database) edited by Dr. Soorya Kabekkodu, International Centre for Diffraction Data, Newtown Square, PA, USA.Google Scholar
Larson, A. C. and Von Dreele, R. B. (2004). General Structure Analysis System (GSAS) (Report LAUR 86-784) Los Alamos National Laboratory.Google Scholar
Lee, P. L., Shu, D., Ramanathan, M., Preissner, C., Wang, J., Beno, M. A., Von Dreele, R. B., Ribaud, L., Kurtz, C., Antao, S. M., Jiao, X., and Toby, B. H. (2008). “A twelve-analyzer detector system for high-resolution powder diffraction,” J. Synchrotron Radiat. 15(5), 427432.CrossRefGoogle ScholarPubMed
Louër, D. and Boultif, A. (2007). “Powder pattern indexing and the dichotomy algorithm,” Z. Kristallogr. Suppl.,” 2007, 191196.CrossRefGoogle Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J., and Wood, P. A. (2008). “Mercury CSD 2.0 – new features for the visualization and investigation of crystal structures,” J. Appl. Crystallogr. 41, 466470.CrossRefGoogle Scholar
McKinnon, J. J., Spackman, M. A., and Mitchell, A. S. (2004). “Novel tools for visualizing and exploring intermolecular interactions in molecular crystals,” Acta Crystallogr., B 60, 627668.CrossRefGoogle ScholarPubMed
Shields, G. P., Raithby, P. R., Allen, F. H., and Motherwell, W. S. (2000). “The assignment and validation of metal oxidation states in the Cambridge Structural Database,” Acta Crystallogr. B, Struct. Sci. 56(3), 455465.CrossRefGoogle ScholarPubMed
Spackman, M. A., and Jayatilaka, D. (2009). “Hirshfeld surface analysis,” CrystEngComm 11, 1932.CrossRefGoogle Scholar
Stephens, P. W. (1999). “Phenomenological model of anisotropic peak broadening in powder diffraction,” J. Appl. Crystallogr. 32, 281289.CrossRefGoogle Scholar
Sutherland, R., Boon, R. J., Griffin, K. E., Masters, P. J., Slocombe, B., and White, A. R. (1985). “Antibacterial activity of mupirocin (pseudomonic acid), a new antibiotic for topical use,” Antimicrob. Agents Chemother. 27(4), 495498.CrossRefGoogle Scholar
Sykes, R. A., McCabe, P., Allen, F. H., Battle, G. M., Bruno, I. J., and Wood, P. A. (2011). “New software for statistical analysis of Cambridge Structural Database data,” J. Appl. Crystallogr. 44, 882886.CrossRefGoogle Scholar
Thompson, P., Cox, D. E., and Hastings, J. B. (1987). “Rietveld refinement of Debye-Scherrer synchrotron X-ray data from Al2O3 ,” J. Appl. Crystallogr. 20(2), 7983.CrossRefGoogle Scholar
van de Streek, J., and Neumann, M. A. (2014). “Validation of molecular crystal structures from powder diffraction data with dispersion-corrected density functional theory (DFT-D),” Acta Crystallogr., B, Struct. Sci., Crystal Eng. Mater. 70(6), 10201032.CrossRefGoogle Scholar
Wang, J., Toby, B. H., Lee, P. L., Ribaud, L., Antao, S. M., Kurtz, C., Ramanathan, M., Von Dreele, R. B., and Beno, M. A. (2008). “A dedicated powder diffraction beamline at the Advanced Photon Source: Commissioning and early operational results,” Rev. Sci. Instrum. 79, 085105.CrossRefGoogle ScholarPubMed
Wavefunction, Inc. (2013). Spartan ‘14 Version 1.1.0, Wavefunction Inc., 18401 Von Karman Ave., Suite 370, Irvine CA 92612.Google Scholar
Wolff, S. K., Grimwood, D. J., McKinnon, M. J., Turner, M. J., Jayatilaka, D., and Spackman, M. A. (2012). Crystal Explorer Version 3.1 (University of Western Australia, Perth, Western Australia).Google Scholar

Kaduk supplementary material

Kaduk supplementary material 1

File 3 MB

Kaduk supplementary material

Kaduk supplementary material 2

File 10 KB

Full text views

Full text views reflects PDF downloads, PDFs sent to Google Drive, Dropbox and Kindle and HTML full text views.

Total number of HTML views: 33
Total number of PDF views: 58 *
View data table for this chart

* Views captured on Cambridge Core between September 2016 - 23rd January 2021. This data will be updated every 24 hours.

Hostname: page-component-76cb886bbf-9l59n Total loading time: 0.482 Render date: 2021-01-23T06:02:44.205Z Query parameters: { "hasAccess": "0", "openAccess": "0", "isLogged": "0", "lang": "en" } Feature Flags: { "shouldUseShareProductTool": true, "shouldUseHypothesis": true, "isUnsiloEnabled": true, "metricsAbstractViews": false, "figures": false, "newCiteModal": false }

Send article to Kindle

To send this article to your Kindle, first ensure no-reply@cambridge.org is added to your Approved Personal Document E-mail List under your Personal Document Settings on the Manage Your Content and Devices page of your Amazon account. Then enter the ‘name’ part of your Kindle email address below. Find out more about sending to your Kindle. Find out more about sending to your Kindle.

Note you can select to send to either the @free.kindle.com or @kindle.com variations. ‘@free.kindle.com’ emails are free but can only be sent to your device when it is connected to wi-fi. ‘@kindle.com’ emails can be delivered even when you are not connected to wi-fi, but note that service fees apply.

Find out more about the Kindle Personal Document Service.

Crystal structure of mupirocin form I, C26H44O9
Available formats
×

Send article to Dropbox

To send this article to your Dropbox account, please select one or more formats and confirm that you agree to abide by our usage policies. If this is the first time you use this feature, you will be asked to authorise Cambridge Core to connect with your <service> account. Find out more about sending content to Dropbox.

Crystal structure of mupirocin form I, C26H44O9
Available formats
×

Send article to Google Drive

To send this article to your Google Drive account, please select one or more formats and confirm that you agree to abide by our usage policies. If this is the first time you use this feature, you will be asked to authorise Cambridge Core to connect with your <service> account. Find out more about sending content to Google Drive.

Crystal structure of mupirocin form I, C26H44O9
Available formats
×
×

Reply to: Submit a response


Your details


Conflicting interests

Do you have any conflicting interests? *