Crystalline Sponge Gallery

G032 · Alkaloid

Peiminine

C27H45NO3 · 431.66 g mol−1

First crystal structure · Angewandte Chemie International Edition 2026 · compound 21 →

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INTERACTIVE 3D STRUCTURE

Explore Peiminine in its crystalline sponge

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CHONCage
2D chemical structure of Peiminine
Peiminine · 2D chemical structure
3D crystal structure of Peiminine determined by the crystalline-sponge method
Peiminine · crystalline-sponge guest structure
Peiminine inside a crystalline sponge coordination cage
Peiminine · coordination-cage host–guest structure

Peiminine resolved by the crystalline-sponge method.

A remarkably intricate steroidal alkaloid with six rings and twelve stereocentres.

Molecular formula
C27H45NO3
Molecular weight
431.66 g mol−1
CCDC accession
2459708 ↗
Host
Pd6L4 cage
Study
Angew. Chem. 2026
Compound in publication
21

MOLECULAR HISTORY

Ninety years from isolation to native-form single crystals

Peiminine belongs to the densely functionalized Fritillaria steroidal alkaloids. Earlier structural work relied on salts, derivatives and powder diffraction because the neutral native compound resisted single-crystal analysis.

  1. 1936

    Early Fritillaria alkaloid isolation

    Chi, Kao and Chang reported the isolation of peimine from Fritillaria roylei, opening the systematic chemical study of this closely related alkaloid family.1

  2. 1968

    Structure studied as a methobromide

    The structure of verticinone methobromide was investigated by X-ray diffraction, illustrating the historical need to convert the alkaloid into a crystalline ionic derivative.2

  3. 1970

    Derivative crystal model refined

    A full crystal and molecular structure of verticinone methyl bromide established detailed stereochemical information for the derivatized alkaloid.3

  4. 2013

    Native material characterized as a powder

    Powder X-ray diffraction supplied unit-cell parameters and a space group for peiminine, but not the complete atomic single-crystal model of the native molecule.4

  5. 2026

    First native-form single crystals

    The crystalline sponge yielded single crystals of native peiminine for the first time and resolved the absolute configurations of all twelve stereocentres.5

WHY THIS STRUCTURE MATTERS

Derivative crystals and powder patterns had supplied important clues, but the native molecule itself had not yielded a complete single-crystal structure. The crystalline-sponge result directly resolves its exceptionally dense stereochemistry.

References

  1. Chi, Y.-F.; Kao, Y. S.; Chang, K. J. “The Alkaloids of Fritillaria roylei. I. Isolation of Peimine.” J. Am. Chem. Soc. 1936, 58, 1306–1307. DOI 10.1021/ja01298a067 ↗
  2. Itô, S.; Fukazawa, Y.; Okuda, T.; Iitaka, Y. “The Structure of Verticinone Methobromide.” Tetrahedron Lett. 1968, 9, 5373–5375. DOI 10.1016/S0040-4039(00)75387-1 ↗
  3. Brisse, F. “The Crystal and Molecular Structure of Verticinone Methyl Bromide.” Acta Crystallogr. B 1970, 26, 171–180. DOI 10.1107/S0567740870002121 ↗
  4. Xiao, D.; Zhang, L. L.; Wu, X. Q.; Yan, J.; Luo, W.; Li, H. “X-ray Powder Diffraction Data for Peiminine.” Powder Diffr. 2013, 28, 312–314. DOI 10.1017/S0885715613000535 ↗
  5. He, W.; Takezawa, H.; Fujita, M. Angew. Chem. Int. Ed. 2026, 65, e202524615. DOI 10.1002/anie.202524615 ↗

SOURCE PUBLICATION

Second-Generation Crystalline Sponges Enabling Consistent Structure Analysis Under Standardized Conditions for Diverse Molecules

Angewandte Chemie International Edition 2026

DOI 10.1002/anie.202524615 ↗