Processes for chemical synthesis of lipochitooligosaccharides

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

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C536S018700, C536S020000, C536S055300

Reexamination Certificate

active

08049002

ABSTRACT:
Processes for the synthesis of lipochitooligosaccharides were developed. A fully acylated oligoglucosamine precursor is prepared and reacted with a glucosamine monomer that has an amine protecting phthaloyl group. With removal of the phthaloyl group, a fatty acid may be added on the terminal glucosamine unit, forming a lipochitooligosaccharide. The processes can be adapted for use on a commercial scale.

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Demont-Caulet et al., Nodule Inducing Activity of SyntheticSinorhizobium meliloti NodulationFactors and Related Lipo-Chitooligosaccharides on Alfalfa. Importance of the Acyl Chain Structure, Plant Physiology, 1999, vol. 120:83-92.
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Ikeshita et al., Preliminary Communication NOD BJ-IV (C 18:1 Fuc Gro) Produced byBradyrhizobium japonicumStrain USDA61, Carbohydrate Research 1995, vol. 266:C1-C6.
Wang et al., Chemical Synthesis of NODRM-1: The Nodulation Factor Involved inRhizobium meliloti-Legume Symbiosis, J. Chem. Soc. Perkin Trans., 1994, vol. 1:623-628.
P. Stangier et al., Solid-Phase Transimidation for the Removal of N-Phthalimido-And-Tetrachlorophthalimido Protecting Groups on Carbohydrates, Synlett., 1996, vol. 2:179-181.
Demont-Caulet et al., Nodule Inducing Activity of SyntheticSinorhizobium melilotiNodulation Factors and Related Lipo-Chitooligosaccharides on Alfalfa. Importance of the Acyl Chain Structure, Plant Physiology, 1999, vol. 120:83-92.

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