Abstract
This review is dedicated to wheat hemicelluloses and its main components d-xylose and l-arabinose as raw materials for fine organic chemistry. The context of the wheat agro-industry, its by-products, and extraction and hydrolysis of hemicelluloses to produce the pentoses are considered. The straightforward preparation of pentose-based surfactants, their properties, and their situation in the field of carbohydrate-based surfactants are addressed. Multistep transformations of pentoses are also described, first from a methodology point of view, with the aim of producing multifunctional enantiopure building-blocks, then considering targeted natural and/or bioactive products. Selected reactions of furfural, an important dehydration product of pentoses, are also presented.
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Abbreviations
- δO/W:
-
Oil/water interfacial tension
- APG:
-
Alkyl polyglucosides
- APP:
-
Alkyl polypentosides
- CMC:
-
Critical micelle concentration
- DP:
-
Degree of polymerization
- d-Xyl:
-
d-Xylose
- GAG:
-
Glycosaminoglycan
- HLB:
-
Hydrophilic–lipophilic balance
- l-Ara:
-
l-Arabinose
- MOE:
-
Modulus of elasticity
- MOR:
-
Modulus of rupture
- MTHF:
-
Methyltetrahydrofuran
- RCM:
-
Ring-closing metathesis
- GAG:
-
Glycosaminoglycan
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Acknowledgments
We are grateful to the CNRS, University of Reims, ARD Company, MESR, Conseil Régional Champagne-Ardenne, Conseil Général de la Marne, Ville de Reims, and Fondation du Site Paris-Reims for providing financial support, and to Europol’Agro (CARINNA) for managing the research program GLYCOVAL. We also warmly thank our co-workers, whose names appear in the references from our labs, for their contributions.
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Martel, F., Estrine, B., Plantier-Royon, R., Hoffmann, N., Portella, C. (2010). Development of Agriculture Left-Overs: Fine Organic Chemicals from Wheat Hemicellulose-Derived Pentoses. In: Rauter, A., Vogel, P., Queneau, Y. (eds) Carbohydrates in Sustainable Development I. Topics in Current Chemistry, vol 294. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2010_54
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