Bioinspired Crystallization of Guanine

Chen, Fenghua; Guo, Dongmei; Gao, Juan; Ma, Yurong

doi:10.1021/acs.jpclett.1c03010

Cited by 17 publications

(16 citation statements)

References 45 publications

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“…Additionally, the crystallization of synthetic β-guanine–hypoxanthine mixed crystals in the β-guanine phase (Figure S10h) agrees with a recent finding that guanine preferentially crystallizes as the β - polymorph when it forms solid solutions with hypoxanthine and xanthine. This suggests that purine additives may stabilize the metastable β-polymorph.…”

Section: Discussionsupporting

confidence: 89%

Biogenic Guanine Crystals Are Solid Solutions of Guanine and Other Purine Metabolites

et al. 2022

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Highly reflective crystals of the nucleotide base guanine are widely distributed in animal coloration and visual systems. Organisms precisely control the morphology and organization of the crystals to optimize different optical effects, but little is known about how this is achieved. Here we examine a fundamental question that has remained unanswered after over 100 years of research on guanine: what are the crystals made of ? Using solution-state and solid-state chemical techniques coupled with structural analysis by powder XRD and solid-state NMR, we compare the purine compositions and the structures of seven biogenic guanine crystals with different crystal morphologies, testing the hypothesis that intracrystalline dopants influence the crystal shape. We find that biogenic “guanine” crystals are not pure crystals but molecular alloys (aka solid solutions and mixed crystals) of guanine, hypoxanthine, and sometimes xanthine. Guanine host crystals occlude homogeneous mixtures of other purines, sometimes in remarkably large amounts (up to 20% of hypoxanthine), without significantly altering the crystal structure of the guanine host. We find no correlation between the biogenic crystal morphology and dopant content and conclude that dopants do not dictate the crystal morphology of the guanine host. The ability of guanine crystals to host other molecules enables animals to build physiologically “cheaper” crystals from mixtures of metabolically available purines, without impeding optical functionality. The exceptional levels of doping in biogenic guanine offer inspiration for the design of mixed molecular crystals that incorporate multiple functionalities in a single material.

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Section: Discussionsupporting

confidence: 89%

Biogenic Guanine Crystals Are Solid Solutions of Guanine and Other Purine Metabolites

et al. 2022

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“…Studies on the role of hypoxanthine in the biomimetic synthesis of guanine crystals have been reported. [31][32][33][34] Hypoxanthine, compared with guanine, has one less amino group. The two most stable tautomers of hypoxanthine in the gas phase are N 7 -hypoxanthine and N 9hypoxanthine, which are similar to guanine (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Solid-state separation of hypoxanthine tautomers through a doping strategy

Xue

Liang

et al. 2022

CrystEngComm

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“…7 Researchers have tried to control the polymorphs, morphologies and orientation of guanine crystals in the laboratory. 8,16,[22][23][24][25][26] Imai and his coworkers controlled the morphology and orientation of AG crystals on a modified glass substrate. 22 Our group realized the synthesis of β-AG, 23 the elongated single crystalline microplatelets of β-AG 27 and twinned β-AG microplatelets doped with hypoxanthine.…”

Section: Introductionmentioning

confidence: 99%