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Alkali-hydrolysis of D-glucono-delta-lactone studied by chiral Raman and circular dichroism spectroscopies

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Abstract

The alkali-hydrolysis of D-glucono-delta-lactone (GDL) was investigated by chiral Raman and circular dichroism (CD) spectroscopies in combination with density functional theory calculation. Based on the characteristic CD bands of GDL and its hydrolysis product, the dynamics of hydrolysis was studied using stopped-flow CD method. Using chiral Raman spectroscopy (CRS), the stereochemical change of GDL owing to the hydrolysis reaction was discussed on the vibrational scale. The CRS results show that the ring-opening due to hydrolysis has a great influence on the chiral structure around the carbonyl group, which was evidenced by the disappearance of the CRS band at 1735 cm 1 (C=O stretching vibrational mode). In addition, the change of positions and intensity of CRS bands was also observed, which was ascribed to the perturbation around the C2, C3, C4 and C5 carbons due to ring-opening. It is worthy to note that the stereochemistry of C2, C3, C4 and C5 had no fundamental change during the hydrolysis reaction, which was reflected in the maintenance of the signs of the CRS bands. Our results demonstrate that in comparison with CD technique, CRS may provide more detailed structural information of chiral molecules and open up new vistas of research for chiral reactions.

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Authors and Affiliations

  1. State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China

    GuoQing Jia, Shi Qiu, GuanNa Li, Jun Zhou, ZhaoChi Feng & Can Li

  2. Graduate University of Chinese Academy of Sciences, Beijing, 100049, China

    GuoQing Jia, Shi Qiu, GuanNa Li & Jun Zhou

Authors
  1. GuoQing Jia
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  2. Shi Qiu
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  3. GuanNa Li
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  4. Jun Zhou
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  5. ZhaoChi Feng
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  6. Can Li
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Correspondence to ZhaoChi Feng or Can Li.

Additional information

Supported by the National Natural Science Foundation of China (Grant Nos. 20621063, 20773123, and 20673110) and Programme for Strategic Scientific Alliances between China and the Netherlands (Grant No. 2008DFB50130) 1) In some reference, chiral Raman spectroscopy (CRS) is also called Raman optical activity (ROA).

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Jia, G., Qiu, S., Li, G. et al. Alkali-hydrolysis of D-glucono-delta-lactone studied by chiral Raman and circular dichroism spectroscopies. Sci. China Ser. B-Chem. 52, 552–558 (2009). https://doi.org/10.1007/s11426-009-0085-0

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  • DOI: https://doi.org/10.1007/s11426-009-0085-0

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