MXPA97009352A - Alpha-hortodionine derivatives with high mettion content - Google Patents
Alpha-hortodionine derivatives with high mettion contentInfo
- Publication number
- MXPA97009352A MXPA97009352A MXPA/A/1997/009352A MX9709352A MXPA97009352A MX PA97009352 A MXPA97009352 A MX PA97009352A MX 9709352 A MX9709352 A MX 9709352A MX PA97009352 A MXPA97009352 A MX PA97009352A
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Abstract
The alpha-hordothionine derivatives carried out by means of the specific substitution at a position with residues of mentionin cause the enrichment of methionine in plant
Description
DERIVATIVES DS a-HORDOTIONINE WITH HIGH METTIONIN CONTENT
DESCRIPTION OF THE INVENTION This invention relates to the improvement of food formulations. Specifically, this invention relates to a-hordothionine derivatives that provide high percentages of the essential amino acid methionine in plants. Food formulations are required to provide the animals with essential nutrients critical for growth. However, crop plants generally become food sources with low nutrional quality. They contain portions of several amino acids that are essential for animals but can not be synthesized by them. For many years researchers have tried to improve the balance of essential amino acids in proteins of important crops through breeding programs. As more is known about the storage of proteins and the expression of the genes that encode those proteins, and they develop a transformation to a greater variety of plants, molecular tests to improve the quality of seed proteins can provide alternative to the more conventional attempts. Thus, the specific levels of amino acids in a given culture can be improved by means of biotechnology.
An alternative method is to express a heterolacta protein of an "amine acid favorable oompaaloian" at levels sufficient to improve enrichment of the feed or forage. For example, several amino acids rich in sulfur have been identified. A key to the good expression of these proteins includes efficient expression cartridges with specific promoters. Not only the regions that control the genes direct the synthesis of high levels of mRNA, the mRNA must be transferred to a stable protein. Among the essential amino acids needed for animal nutrition, often scarce in the crop plants, is methianine, trianinft and Haitta. Attempts to increase the levels of those free amino acids by means of reproduction, mutant selection and / or changing the composition of accumulated storage proteins in the crop plants have had little success. Generally the expression of the transgenic storage protein was too low. The expression cartridge of the Brazil nut promoted with 2S phaseolin is an effect of a chimeric gene specific to the effective seed. However, even through the protein of the Brazil nut increases the total amount of ethionine and bound methionine, improving the nutritional value, there seems to be a threshold limit in regard to the total amount of methionine accumulated in the seeds . Laa aßmillaa continue to favor insufficient methionine sources.
An alternative to improve specific amino acid levels by altering the levels of proteins containing the desired amino acids is the modification of amino acid biosynthesis. The technology of recombinant DNA and generic transfer technologies have been applied to alter the enzymatic activity by catalyzing key stages in the biosynthetic path of the amino acids. Glassman, in U.S. Pat. No. 5,258,300; Galili ßt, al in the European patent application no. 485870; [1992]. However, the modification of the amino acid levels in the seeds is not always correlated with changes in the level of proteins that incorporate these amino acids. Burrow et al., Mo1.Gen.Gane.; vol. 241; p. 431-439 (1993). Although significant increases in free lysine levels in the leaves have been obtained through the selection of the DHSPS mutants or by expressing the DHDPS EiCQlJ in plants, it remains shown that these alterations can increase the bound target amino acids, which represent approximately 90 % or more of the total amino acids »Thus there is a minimal impact on the nutritional value of the seeds. Based on the above there is a need for methods to increase the levels of essential amino acids, ethionine, lißina and threonine in the seeds of plants. It is therefore an object of the present invention to provide methods for genetically modifying plants to increase the levels of the essential amino acid methionine in plants. It is another object of the present invention to provide the seeds for food and / or fodder with higher levels of the essential amino acid methionine than the wild species of the same seeds. It has been determined that a class of compounds, the a-hordothionines can be modified to increase their methionine content. The a-hordothionine is a protein of 45 amino acids that has been well characterized. It can be isolated from barley seeds [Hordeu vulgare]. The molecule is eatabilized by four disulfide bonds resulting from eight cysteine residues. The amino acid sequence as provided in sequence identification no. 1 In its natural form it is especially rich in arginine and lysine, containing 5 residues [10%] of each. However, it does not contain the essential amino acid methionine. The protein has been synthesized and the three-dimensional structure has been determined by means of computer modeling. The molding of the protein predicts that the ten charged residues [arginine at positions 5,10,17,19 and 30, and lysine at positions 1,23,32,38 and 45] all are made on the surface of the molecule. The polar side chains of polar amino acids [asparagine in position 11, glutamine in position 22 and threonine in position 41] are also present on the surface of the molecule. In addition, the hydrophobic amino acids [such as the leucine side chains at positions 8, 15, 24 and 44 and valine at position 18] are also accessible for solvents. The three-dimensional molding of the protein indicates that the arginine residue at position 10 is critical for the retention of the appropriate three-dimensional structure and possible doubling through the hydrogen bonding interactions with the C terminal residue of the protein. . A substitution of methionine at that point would disrupt the hydrogen bonds that include arginine at position 10, serine at position 2 and lysine at position 45, leading to the destabilization of the structure. The synthetic peptide that has this substitution could not bend correctly, which supports this analysis. The conservation of the arginine residues at position 10 provided a protein that was correctly bent. Since methionine is a hydrophobic amino acid, the surface hydrophobic amino acid residues, leucine at positions 8,15 and 33, and valline at position 18, were substituted with methionine. The polar amino acids asparagine in position 11, glutamine in position 22 and threonine in position 41, are substituted with ßthionine. The resulting compound has the sequence indicated in the SEQUENTIAL IDENTIFIED NO. 2. The molecule can be synthesized by synthesis of peptides in solid phase and doubled in a stable structure. It has seven residues of mthionine [15.5%] and includes the eight sisters, the modified propheine has a sulfur amino acid content of 33%. While the IDENTIFIED SEQUENCE does not. 2 is illustrative of the present invention, is not intended to be a limitation. Methionine substitutions can also be made in positions containing charged amino acids. Only the arginine in position 10 is critical to maintain the structure of the protein through a network of hydrogen bonding with lysine in the positions 1,23,32 and / or 38, with arginine in positions 5,17,19 and / or 30 .. The resulting compound has the sequence indicated in the SEQUENTIAL IDENTIFIED NO. 3. The synthesis of the compounds is carried out according to the peptide synthesis methods that are well known in the art and therefore do not form part of the invention. In vitro the compounds have been synthesized and applied to an Applied Biosytems 413a peptidoß synthesizer using fastmocmr chemistries including hbtu [2- (lh-benzotriasiazol-1-yl-1-hexafluorophosphate, 2,3,3-tßtramßtilurino published by
Rao ßt al. Int-J.Pep.Prot.Rea. : vol. 40; p. 508-515;
[1992]. Loe pßptidoß ßß divide according to the standard protocols and ßß purify by means of tto «£ **« inverse using standard methods. The amino acid sequence of each peptide was confirmed by means of automatic Edman degradation in a protein sequencer / analyzer 120a pth 477a from Applied Biosystems. More preferably, however, the compounds of the invention are synthesized in vitro by means of bacterial or plant cells that have been transformed by means of the insertion of an expression cartridge containing a synthetic gene when transcribed and translated to give the desired compound . These empty expression cartridges, which provide the appropriate regulatory sequences for the plant or bacterial expression of the desired sequence, are also well known, and the nucleotide sequence for the synthetic gene, either RNA or DNA, can be easily derived from the amino acid sequence for the protein using standard reference texts. Preferably, these synthetic genes will use codons preferred by plants to improve the expression of the desired protein. The following description exemplifies the compositions of this invention and the methods of preparing and using them. However, it will be understood that other known methods that those of ordinary skill in the art know to be equivalent could also be employed. The genes encoding these compounds can be inserted into appropriate expression cartridges and introduced into cells of plant species. Thus, an especially preferred embodiment of this method includes ßl inserting a DNA sequence encoding a compound of this invention into an appropriate reading frame in the plant genome, together with the transcription initiator and active promoter sequences in the plant . The transcription and translation of the DNA sequence under control of the regulatory sequences cause the expression of the protein sequence at levels that provide a high amount of a protein in the tissues of the plant. Preferred plants to be transformed according to the methods of the invention are cereals including corn, rye, barley, wheat, sorghum, oats, millet, rice, sunflower, alfalfa, rapeseed and soybean. DNA sequences encoding the appropriate amino acid sequence can then be prepared and this synthetic DNA sequence can be inserted into a suitable plant expression cartridge. Likewise, various cartridges and plant expression vectors are well known in the art. With the term "expression cartridge" is implied a complete group of control sequences including initiator, promoter and terminal sequences that function in a plant cell when crossing a structural gene in the appropriate reading frame. The cartridges of frequent expression and preferably contain any assortment of restriction sites suitable for the division ß insertion of any desired structural gene. It is important that the cloned gene has a start codon in the reading frame suitable for the structural sequence. In addition, the plant expression cartridge preferably includes a strong promoter sequence at one end to cause the ene to be transcribed at a high frequency, and a poly-a recognition sequence at the other end for proper processing and transport of the RNA delivery courier. An example of that preferred [empty] expression cartridge in which the cDNA of the present invention can be inserted into the plasmid pPHI414 developed by Beach, et.al., of Pioneer Hi-Bred International, Inc., Johnston, IA, described in the US patent application DO NOT. 07 / 785,648 [1991]. Highly preferred plant expression cartridges will be designed which include one or more selectable marker genes, such as the kanamycin resistance or herbicide tolerance genes. With the term "vector" is meant a DNA sequence that is capable of replicating and expressing a foreign gene in a host cell. Typically, the vector has one or more recognition points of endocrucosease that can be cut in a predisceptible manner by the use of the appropriate enzyme, such vectors are preferably constructed to include structural genetic sequences that impart resistance to antibiotics or herbicides which then serve as markers to identify and separate transformed cells. Preferred labeling / labeling agents include kanamycin, chlorosulfuron, phosphonomycin, hygromycin and metatrezate. A cell in which the foreign genetic material in a vector is functionally expressed has been "transformed" by the vector and is called "transformant". A particularly preferred vector is a plasmid, which involves a circular two-stranded DNA molecule that is not part of the chromosomes of the cell. As mentioned above, both genomic and cDNA encoding the gene of interest in this invention can be used. The vector of interest can be partially constructed from a cDNA clone and partially from a genomic clone. When the gene of interest has been isolated, genetic constructs are made that contain the necessary regulatory sequences that provide efficient expression of the gene in the host cell. According to the invention, the genetic construct will contain [a] a first genetic sequence encoding the protein or characteristic of interest and [b] one or more regulatory sequences that are linked to either side of the structural gene of interest. Typically, regulatory sequences will be selected from the group comprising promoters and terminators. Regulatory sequences can be autologous or biostological sources.
Promoters that can be used in the genetic sequence include the NOS, OCS and CaMV promoters. An efficient plant promoter that can be used is an overproducing plant promoter. The overproducting plant promoters that can be used in the invention include the promoter of the chlorophyll a-β binding protein and the promoter of the small subunit [ss] of ribulose carboxylase-1, 5-biphosphate soy. See for example Berry-Lowe, et. al., J.Molecular and APP.Gen. : vol. 1; p. 483-498; [1982]. These two promoters are known to be induced by light in eukaryotic plant cells. See for example An
Agricultural Perspective, A. Cashmnore, Pelham, New York; p. 29-38; (1983); G. Coruzzi, et. to the. J.Blol.tTh m. : vol. 258; pgs 1399; (1983); and P. Dunsmuir et. al., and AP. Gen I vol. 2; p. 285, [1983]. The expression cartridge contains the structural gene of the protein of this invention operably linked to the desired control sequences can be ligated into a suitable cloning vector. In general, plasmid or viral [bacteriophage] vectors containing replication and control sequences derived from the species compatible with the host cell are used. The cloning vector will typically carry a replication origin if as specific genes that are capable of providing phosphotyping selection markers in the transformed host cell. Typically, the genes that confer resistance to selected antibiotics or herbicides are used. After the genetic material is introduced into the target cells, the transformed cells and / or colonies of the cells can be isolated by selection based on those markers. Typically, an intermediate host cell will be used in the practice of the invention to increase the copy number of the cloning vector. With a large number of copies, the vector containing the gene of interest can be isolated in important quantities to enter the plant cells. Plant cells that can be used in the practice of the invention include prokaryotes, including bacterial hosts such as E.CQli, S.Tvphiirmr-him. Y
Be tia marcescena. Eukaryotic hosts such as yeast or fungal filaments can also be used in this invention. And that these hosts are also microorganisms will be essential to ensure that plant promoters that do not cause the expression of the protein in the bacteria are used in the vector. The isolated cloning vector will then be introduced into the plant cell using any convenient technique including electroporation [in protoplatoa], retrovirua, bombardment and microinjection in cells of monocotiledoneaß or dicotilendoneaß plants in cell or tissue cultures to provide transformed plant cells which contain as Foreign DNA at least one copy of the DNA sequence of the plant expression cartridge. Preferably the monocotyledonous species will be selected from corn, sorghum, wheat or rice, and the dicotyledonous species will be selected from soybeans, alfalfa, rapeseed, sunflower or tomato. Using known techniques the protoplasts can be regenerated and the cell or protein culture can be regenerated to form whole fertile plants which carry and express the gene for a protein according to the invention. Accordingly, a highly preferred embodiment of the present invention is a transformed corn plant, which cells contain as foreign DNA at least one copy of the DNA sequence of an expression cartridge of this invention. Also those of ordinary skill in the art will appreciate that the plant vectors provided herein can be incorporated into aarohacterium turnefac, which can be used to transfer the vector into susceptible plant cells, mainly of dicotyledonous species. Thus, the invention provides a method for increasing the levels of methionine in dicotyledonous plants susceptible to aarobacterium tu efaclena in which the expression cartridges are introduced into the cells by infecting the cells with Agrnbacterium tumefaceras *, of which a plasmid has been modified to include a plant expression cartridge of the invention.
LIST OF THE SEQUENCE [1] GENERAL INFORMATION: [i] APPLICANT: PIONNER HI-BRED INTERNATIONAL, INC. [ii] TITLE OF THE INVENTION: DERIVATIVES OF α-HORDOTIONIN WITH HIGH CONTENT OF METIONI A [iii] SEQUENCE NUMBER: 3 [iv] ADDRESS FOR CORRESPONDENCE [TO] RECIPIENT: PIONNER HI-BRED INTERNATIONAL, INC. [B] ADDRESS: 700 Capital Square, 400 Locust Street [C] CITY: Des Moines [D] STATE: Iowa [E] COUNTRY: USA [F] POSTAL CODE: 50309 [v] LEGIBLE FORM FOR THE COMPUTER: [A] TYPE OF MEDIUM: Flexible disk [B] COMPUTER: IBM compatible PC [C] OPERATING SYSTEM: PC-DOS / MS-DOS [D] SOFTWARE: Patentln Realease # 1.0, version # 1.30 [vi] CURRENT APPLICATION DATA: [A] APPLICATION NUMBER: PCT: [B] SUBMISSION DATE: [C] CLASSIFICATION: [vii] INFORMATION ABOUT THE LAWYER / AGENT: [A] NAME: Simón, Soma G. [B] REGISTRATION NUMBER: 37,444 [C] REFERENCE NUMBER / DOCUMENT: 355-PCT [2] INFORMATION FOR SEQ ID NO.:l: [i] CHARACTERISTICS OF THE SEQUENCE : [A] LENGTH: 45 amino acids [B] TYPE: amino acid [C] TOPOLOGY: linear [XI] DESCRIPTION OF THE SEQUENCE: SEQ ID NO. 1: Lys Ser Cys Cys Arg Ser Thr Leu Gly Arg Asn Cys Tyr Asn Leu Cys 1 5 10 15 Arg Val Arg Gly Wing Gln Lys Law Cys Wing Gly Val Cys Arg Cys Lys 20 25 30 Leu Thr Ser Ser Gly Lys Cys Pro Thr Gly Phe Pro Lys 35 40 45 [2] INFORMATION FOR SEQ ID NO .: 2: [i] CHARACTERISTICS OF THE SEQUENCE: tA] LENGTH: 45 amino acids [B] TYPE: amino acid [D] TOPOLOGY: linear [XI] DESCRIPTION OF THE SEQUENCE: SEQ ID NO. 2: Lys Ser Cys Cys Arg Ser Thr Mßt Gly Arg Mßt Cys Tyr Aan Mßt Cya
1 5 10 15
Arg Met Arg Gly Met Wing Lyß Leu Cyß Wing Gly Val Cyß Arg Cyß Lys 20 25 30 Mßt Thr Ser Ser Gly Lya Cya Pro Met Gly Pha Pro Lya 35 40 45 [2] INFORMATION FOR SEQ ID NO .: 3: [A ] LENGTH: 45 amino acids [B] TYPE: amino acid [D] TOPOLOGY: linear [XI] DESCRIPTION OF THE SEQUENCE: SEQ ID NO. 3: Met Ser Cys Cys Met Ser Thr Met Gly Arg Met Cys Tyr Asn Met Cys 1 5 10 15
Met Met Met Gly Met Met Met Met Cys Ala Gly Val Cys Met Met Cys Met 20 25 Met 30 Met Thr Ser Met Met Met Met Gly Phe Pro Lys 35 40 45
Claims (20)
- CLAIMS 1.- A protein that has the sequence with the SEQUENCE IDENTIFICATION NO. 3 in which the amino acid residues in one or more of positions 1,5,8,11,15,17, 18,19,22,23,24,30,32,33,38 and 41 are methionine and the rest of the residues in those positions are the residues of the corresponding positions in the IDENTIFICATION OF SEQUENCE NO. 1.
- 2. A protein according to claim 1 in which one or more of the amino acid residues in 8,11,15,18, 22,33 and 41 are methionine.
- 3. A protein according to claim 2 in which at least 3 of the amino acid residues at positions 8, 11, 15, 18, 22, 33 and 41 are methionine.
- 4. A protein according to claim 3 in which at least 5 of the amino acid residues at positions 8,11,15,18, 22,33 and 41 are methionine.
- 5. A nucleotide sequence that encodes a protein that has the sequence corresponding to the SEQUENCE IDENTIFICATION NO. 2, in which the amino acid residues in one or more of the β position1,5,8,11,15,17,18,19,22,23,24,30, 32,33,38 and 41 are methionine and the The remainder of the residues in eßaß positions are the residues of the corresponding positions in the SEQUENCE IDENTIFICATION NO. 1.
- 6.- An RNA sequence that encodes a protein that has the sequence corresponding to the SEQUENCE IDENTIFICATION NO. 2, in which the amino acid residues in one or more of the positions 1,5,8,11,15,17,18,19,22,23,24,30, 32,33,38 and 41 are methionine and the The remainder of the residues in those positions are the residues of the corresponding positions in the IDENTIFICATION OF SEQUENCE NO. 1.
- 7.- A DNA sequence that encodes a protein that has the sequence corresponding to the SEQUENCE IDENTIFICATION NO. 3, in which amino acid residues in one or more of positions 1,5,7,8,11,15,17,18,19,22,23,24,30, 32,33,38 and 41 are threonine and the rest of the residues in those positions are the residues of the corresponding positions in the IDENTIFICATION OF SEQUENCE NO. 1.
- 8. An expression cartridge containing the DNA sequence according to claim 7 operably linked to the regulatory sequences of the plant that causes the expression of the DNA sequence in the cells of the plant.
- 9. A bacterial transformation vector consisting of an expression cartridge according to claim 8, operatively linked to the regulatory βßßcuenciaeffective β of bacterial expression that cause replication of the expression cartridge in the β-bacterial cells.
- 10. Bacterial cells containing as foreign plasmid at least one copy of a bacterial transformation vector according to claim 9.
- 11. Transformed plant cells containing at least one copy of the expression cartridge according to claim 8.
- 12. The transformed plant cells according to claim 11, wherein the cells are of a monocotyledone species.
- 13. The transformed plant cells according to claim 11, wherein the cells are selected from the group consisting of corn, sorghum, wheat and rice cells.
- 14. The transformed plant cells according to claim 11, in which the cells are of a dicotyledonous species.
- 15. The transformed plant cells according to claim 14, wherein the cells are selected from the group consisting of soy, alfalfa, rapeseed, sunflower, tobacco and tomato cells.
- 16. A cell or corn tissue culture consisting of cells according to claim 13.
- 17. A method for improving the threonine content of a plant cell or seed comprising the step of expressing a protein proton. according to claim 1 in the cell or seed.
- 18. A method according to claim 17 in which the plant is a dicotyledonous plant.
- 19. A method according to claim 17 in which the plant ßß a monocotyledone plant.
- 20. - The method according to claim 19 by means of which the methionine content of the seed of the plant is improved.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US46044095A | 1995-06-02 | 1995-06-02 | |
US460440 | 1995-06-02 | ||
PCT/US1996/008220 WO1996038563A1 (en) | 1995-06-02 | 1996-05-31 | HIGH METHIONINE DERIVATIVES OF α-HORDOTHIONIN |
Publications (2)
Publication Number | Publication Date |
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MXPA97009352A true MXPA97009352A (en) | 1998-02-01 |
MX9709352A MX9709352A (en) | 1998-02-28 |
Family
ID=23828714
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
MX9709352A MX9709352A (en) | 1995-06-02 | 1996-05-31 | HIGH METHIONINE DERIVATIVES OF 'alpha'-HORDOTHIONIN. |
Country Status (12)
Country | Link |
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US (1) | US5885802A (en) |
EP (1) | EP0832235A1 (en) |
JP (1) | JPH11506329A (en) |
CN (1) | CN1192239A (en) |
AR (1) | AR004938A1 (en) |
AU (1) | AU707354B2 (en) |
BR (1) | BR9609299A (en) |
CA (1) | CA2222600A1 (en) |
HU (1) | HUP9900878A2 (en) |
MX (1) | MX9709352A (en) |
PL (1) | PL323635A1 (en) |
WO (1) | WO1996038563A1 (en) |
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AU661334B2 (en) * | 1991-08-09 | 1995-07-20 | E.I. Du Pont De Nemours And Company | Synthetic storage proteins with defined structure containing programmable levels of essential amino acids for improvement of the nutritional value of plants |
DE69332974T2 (en) * | 1992-03-19 | 2004-05-19 | E.I. Du Pont De Nemours And Co., Wilmington | NUCLEIC ACID FRAGMENTS AND METHOD FOR INCREASING THE LYSINE AND THREONINE CONTENT OF THE PLANT SEEDS |
WO1994010315A2 (en) * | 1992-10-23 | 1994-05-11 | Pioneer Hi-Bred International, Inc. | Process for enhancing the content of a selected amino acid in a seed storage protein |
EP0745126B1 (en) * | 1993-01-13 | 2001-09-12 | Pioneer Hi-Bred International, Inc. | High lysine derivatives of alpha-hordothionin |
EP0687303B1 (en) * | 1993-03-02 | 2002-11-20 | E.I. Du Pont De Nemours And Company | Increase of the level of methionin in plant seeds by expression of 10kd zein from corn |
US5703049A (en) * | 1996-02-29 | 1997-12-30 | Pioneer Hi-Bred Int'l, Inc. | High methionine derivatives of α-hordothionin for pathogen-control |
-
1996
- 1996-05-31 PL PL96323635A patent/PL323635A1/en unknown
- 1996-05-31 CA CA002222600A patent/CA2222600A1/en not_active Abandoned
- 1996-05-31 EP EP96916884A patent/EP0832235A1/en not_active Withdrawn
- 1996-05-31 BR BR9609299A patent/BR9609299A/en not_active Application Discontinuation
- 1996-05-31 WO PCT/US1996/008220 patent/WO1996038563A1/en not_active Application Discontinuation
- 1996-05-31 CN CN96195938A patent/CN1192239A/en active Pending
- 1996-05-31 AU AU59611/96A patent/AU707354B2/en not_active Ceased
- 1996-05-31 JP JP8536728A patent/JPH11506329A/en active Pending
- 1996-05-31 MX MX9709352A patent/MX9709352A/en unknown
- 1996-05-31 HU HU9900878A patent/HUP9900878A2/en unknown
- 1996-05-31 AR ARP960102843A patent/AR004938A1/en unknown
-
1997
- 1997-03-26 US US08/824,382 patent/US5885802A/en not_active Expired - Lifetime
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