Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Statutory Invention Registration
1991-05-21
2002-10-01
Carone, Michael J. (Department: 3641)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
C536S118000
Statutory Invention Registration
active
H0002050
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
&bgr;-carrageenan, which is understood to be the idealized, nonsulfated member of the carrageenan family and the D,D-stereoisomer of agarose, consists of multiple units of carrabiose. Carrabiose contains 1,3-linked &bgr;-D-galactopyranose and 1,4-linked 3,6 anhydro &agr;-D-galactopyranose units. &bgr;-carrageenan has been reported to occur in segments of natural carrageenans from marine macroalgae, but has never been isolated in pure or even in purified form where the sulfate ester content is less than 2% by weight.
2. Statement of Related Art
In an article by Greer et al., “Characterization of Hybrid (Beta-Kappa-Gamma) Carrageenan from
Eucheuma gelatinae
J. Agardh (Rhodophyta, Solieriaceae) Using Carrageenases, Infrared and
13
C-Nuclear Magnetic Resonance Spectroscopy”, Botanica Marina, XXVII:473-478 (1984), components of carrageenan from
Eucheuma gelatinae
were identified, including the presence of &bgr;-carrageenan and &ggr;-carrageenan (a 6-sulfate precursor of &bgr;-carrageenan) using analytical techniques such as infrared and
13
C-nuclear magnetic resonance, and the use of carrageenases.
Mollion et al., “
13
C NMR study of the heterogeneity of the carrageenan from
Rissoella verruculosa
(Bert.) J. Ag. (Rhodophtya)”, Food Hydrocolloids, 1:413-421 (1987) conducted a
13
C-NMR study of carrageenan obtained from
Rissoella verruculosa
and obtained several fractions using fractionation techniques. All fractions contained relatively high levels of sulfate, and Mollion, et al. make it clear that they could not separate &bgr;- from &ohgr;-carrageenan by DEAE Sephadex® fractionation. See page 420, second paragraph under Table III.
Shi et al., “
13
C-NMR Spectroscopic Analysis of Carrageenans from Chinese Eucheuma Species”, Oceanologia et Limnoligia Sinica, 18, 3:265-272 (1987), in English translation, determined the compositions and structures of carrageenans without purification (including &bgr;-hybrids) from several species of Eucheuma using
13
C-NMR spectroscopic analysis.
Zablackis et al., “The Carrageenan of
Catenella nipae
Zanard., a Marine Red Alga”, Botanica Marina, XXIX:319-322 (1986), identified carrageenan from the red alga
Catenella nipae
Zanard as &agr;-carrageenan in which the 1,4-linked units consist entirely of 3,6- anhydrogalactose 2-sulfate and the 1,3-linked galactose units are not sulfated, and illustrates structures of the “&bgr;- family”.
Summary of the Invention
Processes have now been discovered for the preparation of both purified &bgr;-carrageenan, i.e. &bgr;-carrageenan containing from 1% to less than 2% by weight of sulfate ester, and substantially pure &bgr;-carrageenan, i.e. &bgr;-carrageenan containing less than 1% by weight of sulfate ester.
Purified &bgr;-carrageenan can be prepared by reacting a marine macroalga that contains &bgr;-carrageenan and/or a precursor thereof with an alkaline compound to convert a precursor present to &bgr;-carrageenan, extracting carrageenan from the macroalga, treating the extracted carrageenan with an aqueous quaternary ammonium salt to form a precipitate and an aqueous solution, separating the solution from the precipitate, and isolating purified &bgr;-carrageenan from the solution.
The substantially pure &bgr;-carrageenan is obtained from the above purified carrageenan by treating an aqueous solution of purified carrageenan with an insoluble ion exchange agent that selectively removes the more highly sulfate ester-containing carrageenans from the solution, and extracting substantially pure &bgr;-carrageenan from the solution remaining after separation of the ion exchange agent.
This invention also comprises purified and substantially pure &bgr;-carrageenan per se.
REFERENCES:
Enzyme Nomenclature, Academic Press, San Diego, California, pp. 356-357 (1992) (month unavailable).*
Websters New Collegiate Dictionary, G. & C. Merriam Company, 1977 (month unavailable) pp. 585.*
Webster's New International Dictionary of the English Language, Merriam-Webster (1956) (month unavailable) pp. 2015.*
Greer et al., “Characterization of Hybrid (Beta-Kappa-Gamma) Carrageenan fromEucheuma gelatinaeJ. Agardh (Rhodophyta, Solieriaceae) Using Carrageenases, Infrared and13C-Nuclear Magnetic Resonance Spectroscopy”, Botanica Marina, XXVII:473-478 (1984).
Mollion, et al., “13C NMR study of the heterogeneity of the carrageenan from Rissoella verruculosa (Bert.) J.Ag. (Rhodophtya)”, Food Hydrocolloids, 1:413-421 (1987).
Shi et al., “13C-NMR Spectroscopic Analysis of Carrageenans from Chinese Eucheuma Species” Oceanologia et Limnoligia Sinica, 18, 3:265-272 (1987).
Zablackis et al., “The Carrageenan ofCatenella nipaeZanard., a Marine Red Alga” Botanica Marina, XXIX:319-322 (1986).
Dumont Lisa E.
Parent Charles A.
Renn Donald W.
Santos Gertrudes A.
Baker Aileen J.
Carone Michael J.
FMC Corporation
Monroe Bruce M.
Ratner & Prestia
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