US3509025A - Method and agent for the enzymatic determination of glucose - Google Patents
Method and agent for the enzymatic determination of glucose Download PDFInfo
- Publication number
- US3509025A US3509025A US571416A US3509025DA US3509025A US 3509025 A US3509025 A US 3509025A US 571416 A US571416 A US 571416A US 3509025D A US3509025D A US 3509025DA US 3509025 A US3509025 A US 3509025A
- Authority
- US
- United States
- Prior art keywords
- phosphate
- glucose
- fructose
- determination
- acyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 title description 50
- 239000008103 glucose Substances 0.000 title description 50
- 238000000034 method Methods 0.000 title description 24
- 230000002255 enzymatic effect Effects 0.000 title description 10
- 239000003795 chemical substances by application Substances 0.000 title description 8
- 229910019142 PO4 Inorganic materials 0.000 description 65
- 239000010452 phosphate Substances 0.000 description 61
- 235000021317 phosphate Nutrition 0.000 description 61
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 48
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 36
- -1 TPNH-oxidase Proteins 0.000 description 31
- 229930091371 Fructose Natural products 0.000 description 21
- 239000005715 Fructose Substances 0.000 description 21
- 229960002737 fructose Drugs 0.000 description 21
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 20
- 229940088598 enzyme Drugs 0.000 description 13
- 102000004190 Enzymes Human genes 0.000 description 12
- 108090000790 Enzymes Proteins 0.000 description 12
- LIPOUNRJVLNBCD-UHFFFAOYSA-N acetyl dihydrogen phosphate Chemical compound CC(=O)OP(O)(O)=O LIPOUNRJVLNBCD-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- SYLLWWIXOMLOPY-UHFFFAOYSA-N benzoyl phosphate Chemical compound OP(O)(=O)OC(=O)C1=CC=CC=C1 SYLLWWIXOMLOPY-UHFFFAOYSA-N 0.000 description 9
- ZKHQWZAMYRWXGA-KQYNXXCUSA-N Adenosine triphosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-N 0.000 description 8
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 8
- XJLXINKUBYWONI-NNYOXOHSSA-N NADP zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-NNYOXOHSSA-N 0.000 description 8
- FFQKYPRQEYGKAF-UHFFFAOYSA-N carbamoyl phosphate Chemical compound NC(=O)OP(O)(O)=O FFQKYPRQEYGKAF-UHFFFAOYSA-N 0.000 description 8
- 102100031126 6-phosphogluconolactonase Human genes 0.000 description 7
- 108010029731 6-phosphogluconolactonase Proteins 0.000 description 7
- VFRROHXSMXFLSN-UHFFFAOYSA-N Glc6P Natural products OP(=O)(O)OCC(O)C(O)C(O)C(O)C=O VFRROHXSMXFLSN-UHFFFAOYSA-N 0.000 description 7
- 108010018962 Glucosephosphate Dehydrogenase Proteins 0.000 description 7
- 102000005548 Hexokinase Human genes 0.000 description 7
- 108700040460 Hexokinases Proteins 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- NBSCHQHZLSJFNQ-GASJEMHNSA-N D-Glucose 6-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O NBSCHQHZLSJFNQ-GASJEMHNSA-N 0.000 description 6
- ACFIXJIJDZMPPO-NNYOXOHSSA-N NADPH Chemical class C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](OP(O)(O)=O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 ACFIXJIJDZMPPO-NNYOXOHSSA-N 0.000 description 6
- 102000004357 Transferases Human genes 0.000 description 6
- 108090000992 Transferases Proteins 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 229940045189 glucose-6-phosphate Drugs 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 235000015203 fruit juice Nutrition 0.000 description 4
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 102000005731 Glucose-6-phosphate isomerase Human genes 0.000 description 3
- 108010070600 Glucose-6-phosphate isomerase Proteins 0.000 description 3
- 108091000080 Phosphotransferase Proteins 0.000 description 3
- 229960001456 adenosine triphosphate Drugs 0.000 description 3
- 238000006911 enzymatic reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 102000020233 phosphotransferase Human genes 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BIRSGZKFKXLSJQ-SQOUGZDYSA-N 6-Phospho-D-gluconate Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O BIRSGZKFKXLSJQ-SQOUGZDYSA-N 0.000 description 2
- GSXOAOHZAIYLCY-UHFFFAOYSA-N D-F6P Natural products OCC(=O)C(O)C(O)C(O)COP(O)(O)=O GSXOAOHZAIYLCY-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 2
- 108010050375 Glucose 1-Dehydrogenase Proteins 0.000 description 2
- 108010063907 Glutathione Reductase Proteins 0.000 description 2
- 102100036442 Glutathione reductase, mitochondrial Human genes 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 235000016954 Ribes hudsonianum Nutrition 0.000 description 2
- 240000001890 Ribes hudsonianum Species 0.000 description 2
- 235000001466 Ribes nigrum Nutrition 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000000378 dietary effect Effects 0.000 description 2
- 229940079919 digestives enzyme preparation Drugs 0.000 description 2
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- FMNMEQSRDWIBFO-UHFFFAOYSA-N propanoyl phosphate Chemical compound CCC(=O)OP(O)(O)=O FMNMEQSRDWIBFO-UHFFFAOYSA-N 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- GXIURPTVHJPJLF-UWTATZPHSA-N 2-phospho-D-glyceric acid Chemical compound OC[C@H](C(O)=O)OP(O)(O)=O GXIURPTVHJPJLF-UWTATZPHSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 108010092060 Acetate kinase Proteins 0.000 description 1
- KIIIREFOSCEENF-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)NCC(=O)OP(O)(O)=O Chemical compound C(C1=CC=CC=C1)(=O)NCC(=O)OP(O)(O)=O KIIIREFOSCEENF-UHFFFAOYSA-N 0.000 description 1
- NBSCHQHZLSJFNQ-QTVWNMPRSA-N D-Mannose-6-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O NBSCHQHZLSJFNQ-QTVWNMPRSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- KTVPXOYAKDPRHY-SOOFDHNKSA-N D-ribofuranose 5-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O KTVPXOYAKDPRHY-SOOFDHNKSA-N 0.000 description 1
- 108010015776 Glucose oxidase Proteins 0.000 description 1
- 239000004366 Glucose oxidase Substances 0.000 description 1
- BUEFQXUHTUZXHR-LURJTMIESA-N Gly-Gly-Pro zwitterion Chemical compound NCC(=O)NCC(=O)N1CCC[C@H]1C(O)=O BUEFQXUHTUZXHR-LURJTMIESA-N 0.000 description 1
- 241000588915 Klebsiella aerogenes Species 0.000 description 1
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 description 1
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 description 1
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 description 1
- DRBBFCLWYRJSJZ-UHFFFAOYSA-N N-methyl-N-phosphonocarbamimidoyl-glycine Natural products OC(=O)CN(C)C(=N)NP(O)(O)=O DRBBFCLWYRJSJZ-UHFFFAOYSA-N 0.000 description 1
- 229910018828 PO3H2 Inorganic materials 0.000 description 1
- 102000011755 Phosphoglycerate Kinase Human genes 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 101001099217 Thermotoga maritima (strain ATCC 43589 / DSM 3109 / JCM 10099 / NBRC 100826 / MSB8) Triosephosphate isomerase Proteins 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 1
- RNBGYGVWRKECFJ-ZXXMMSQZSA-N alpha-D-fructofuranose 1,6-bisphosphate Chemical compound O[C@H]1[C@H](O)[C@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O RNBGYGVWRKECFJ-ZXXMMSQZSA-N 0.000 description 1
- LKDRXBCSQODPBY-ZXXMMSQZSA-N alpha-D-fructopyranose Chemical compound OC[C@]1(O)OC[C@@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-ZXXMMSQZSA-N 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- WQZGKKKJIJFFOK-DVKNGEFBSA-N alpha-D-glucose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- BGWGXPAPYGQALX-ARQDHWQXSA-N beta-D-fructofuranose 6-phosphate Chemical compound OC[C@@]1(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O BGWGXPAPYGQALX-ARQDHWQXSA-N 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000332 continued effect Effects 0.000 description 1
- 239000012470 diluted sample Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 229940025237 fructose 1,6-diphosphate Drugs 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 229960003082 galactose Drugs 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 229940116332 glucose oxidase Drugs 0.000 description 1
- 235000019420 glucose oxidase Nutrition 0.000 description 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N glycerol 1-phosphate Chemical compound OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940041290 mannose Drugs 0.000 description 1
- 229950006780 n-acetylglucosamine Drugs 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- NPSIAHHANQRSIB-UHFFFAOYSA-N oxolane-2,5-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1CCC(=O)O1 NPSIAHHANQRSIB-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/02—Food
- G01N33/14—Beverages
- G01N33/143—Beverages containing sugar
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/54—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving glucose or galactose
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/823—Acetobacter
Definitions
- This invention relates to a method and agent for use in the enzymatic determination of glucose.
- Analytical methods involving enzymes are, in general, characterized by their high substrate specificity and allow for the exact determination of the substrate in the presence of most accompanying materials which are characterized by similar constitution and which represent disturbing fac tors in the same determination using non-enzymatic analytical methods.
- Enzymatic methods for the determination of glucose have also already been proposed and introduced into practice and include, for example, the reaction of glucose with glucose oxidase yielding D-gluconic acid and hydrogen peroxide and the reaction with hexokinase and adenosine triphosphate producing glucose-6-phosphate.
- the reaction products produced, i.e., hydrogen peroxide and glucose-6- phosphate, thereupon are converted in a further reaction into products which can be measured colorimetrically or photometrically (of M. W. Slein in H. U. Bergmeyers Methoden der enzymatischen Analyse, Verlag Chemie, Weinheim, 1962, page 117; and H. U. Bergmeyer and E. Bernt, loc. cit., page 123).
- phosphate donor for the new enzyme there can, according to the invention, be used not only the acetyl phosphate mentioned by Kamel et al. (supra) but also all phosphates having the following formula:
- R is an organic radical, which does not possess a negative charge in the immediate vicinity of the phosphate group.
- the new enzyme is, therefore, best designated acyl phosphate :glucose-6-phosphotransferase.
- the enzyme i.e., acyl phosphate:glucose transferase preferentially reacts with those phosphate donors in which the eifect of a negative charge which may be present on the bond phosphate donor-enzyme is the smallest; see, for example, glutaroyl phosphate, succinyl phosphate and 3 phosphoglyceric acid-l-phosphate in comparison with benzoyl phosphate.
- benzoyl phosphate is employed as phosphate donor, the enzyme reacts more rapidly than it does with acetyl phosphate.
- R is an organic radical, which radical does not possess a negative charge in the immediate vicinity of the phosphate group, and, as transferase, there is used acyl phosphate glucose-6-phosphotransferase.
- the course of the reaction in the process according acyl phosphate glucoseG-phosphotransferese (triphnsphopyridinenucleotide) (fi-phosphogluconic acid) 6PG TPNH H+
- the new agents according to the present invention for use in the determination of glucose comprise a phosphate donor, a transferase, glucose-6-phosphate-dehydrogenase and triphosphopyridine-nucleotide and, advantageously, a buffer.
- the phosphate donor forming a component of the new agent is a phosphate having the Formula I and the transferase is acyl phosphate:glucose-6-phosphotransferase.
- the sample to be investigated is mixed with an acyl phosphate having the Formula I, triphosphopyridinenucleotide (TPN), a buffer (as for example, glycocoll buffer, triethanolamin buffer and tris-buffer) and glucose- 6-phosphate-dehydrogenase.
- TPN triphosphopyridinenucleotide
- a buffer as for example, glycocoll buffer, triethanolamin buffer and tris-buffer
- glucose- 6-phosphate-dehydrogenase glucose- 6-phosphate-dehydrogenase.
- Any glucose 6 phosphate which may be present will now react and can be determined beforehand.
- the acyl phosphate:glucose-6-phosphotransferase is then added and, after some minutes, the glucose is determined photometrically on the basis of the reduced triphosphopyridine nucleotide (TPNH) formed in the ensuing reaction.
- TPNH triphosphopyridine nucleotide
- the preferred range of pH is between 8 and 9.5 and
- acyl phosphates of Formula I which are, after all, mixed acid anhydrides, can only be stored for a limited period of time
- the acyl phosphate required for use in a routine procedure can advantageously be synthesized immediately before theglucose determination in a preceding enzymatic reaction, preferably in the cuvette being used for the photometric determination.
- acetyl phosphate can be prepared from a stable acetate and ATP utilizing acetate-kinase and carbamyl phosphate can be prepared from carbamic acid and ATP using therefor carbamate-phosphokinase.
- An especial advantage of the process according to the present invention in the enzymatic determination of glucose, in comparison with the previously known processes, is the high substrate specificity of the combination of acyl phosphate: glucose 6 phosphotransferase with glucose-6-phosphate-dehydrogenase.
- Reagents End concentration 2.50 ml. of glycocoll bulfer having a pH of 9.0 (200 mM.) mM 0.10 ml. TPN (11 mM.; 10 mg./ml.) mM 0.37 0.10 ml. carbamyl phosphate (140 mM.; 20
- EXAMPLE 3 Glucose determination with nicotoyl phosphate The measurement procedure was carried out as in Example 1 but using nicotoyl phosphate (end molarity 3.3 mM.) in place of the carbamyl phosphate. In this case, a 0.01 M a-D-glucose solution was prepared and analyzed. In the glucose determination, there were used 0.02
- acyl phosphate Mg percent glucose-6ph0sphowith HK/ Deviation, transferase G G-PDH percent EXAMPLE 6
- fructose was determined by the method of H. Klotzsch and H. U. Bergmeyer (cf. H. U. Bergmcycr, Methoden der enzymatischen Analyse,
- R is an organic radical which does not possess a negative charge in the vicinity of the phosphate group and acyl phosphate:glucose-6-phosphotransferase, thereafter reacting the glucose-6-phosphate formed with triphosphopyridinenucleotide (TPN) and glucoSe-6-phosphate-dehydrogenase to form reduced triphosphopyridine nucleotide and spectrophotometrically determining the glucose present on the basis of the reduced triphosphopyridine-nucleotide.
- TPN triphosphopyridinenucleotide
- glucoSe-6-phosphate-dehydrogenase glucoSe-6-phosphate-dehydrogenase
- said phosphate donor is a member selected from the group consisting of benzoyl phosphate, carbamyl phosphate, nicotoyl phosphate, acetyl phosphate, propionyl phosphate, and N- benzoyl-glycol phosphate.
- An agent for use in the enzymatic determination of glucose in a sample containing glucose and fructose which comprises a phosphor donor selected from the group consisting of nicotoyl phosphate and benzoyl phosphate; acyl phosphate:glucose-6-phosphotransferase; glucose-6-phosphate-dehydrogenase; and triphosphopyridine-nucleotide.
- Agent according to claim 7 additionally containing a buffer.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Food Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Immunology (AREA)
- Biochemistry (AREA)
- Zoology (AREA)
- Physics & Mathematics (AREA)
- Genetics & Genomics (AREA)
- Pathology (AREA)
- Microbiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Emergency Medicine (AREA)
- General Physics & Mathematics (AREA)
- Biophysics (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Interface Circuits In Exchanges (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19511598067 DE1598067A1 (de) | 1951-01-28 | 1951-01-28 | Verfahren und diagnostische Mittel zur enzymatischen Bestimmung von Glucose |
| DEB0083297 | 1965-08-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3509025A true US3509025A (en) | 1970-04-28 |
Family
ID=25753451
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US571416A Expired - Lifetime US3509025A (en) | 1951-01-28 | 1966-08-10 | Method and agent for the enzymatic determination of glucose |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3509025A (en, 2012) |
| JP (1) | JPS503674B1 (en, 2012) |
| BE (1) | BE685538A (en, 2012) |
| CH (1) | CH488186A (en, 2012) |
| DE (1) | DE1598067A1 (en, 2012) |
| GB (1) | GB1108770A (en, 2012) |
| NL (1) | NL6611550A (en, 2012) |
| NO (1) | NO117818B (en, 2012) |
| SE (1) | SE337492B (en, 2012) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0043181A1 (en) * | 1980-05-26 | 1982-01-06 | Unitika Ltd. | Measuring composition containing enzymes |
| EP0119722A3 (en) * | 1983-02-16 | 1986-03-05 | Unitika Ltd. | Measuring composition |
| US5426032A (en) * | 1986-08-13 | 1995-06-20 | Lifescan, Inc. | No-wipe whole blood glucose test strip |
| WO2002064819A1 (en) * | 2001-02-14 | 2002-08-22 | International Reagents Corporation | Novel assay method |
| US6458326B1 (en) | 1999-11-24 | 2002-10-01 | Home Diagnostics, Inc. | Protective test strip platform |
| US6525330B2 (en) | 2001-02-28 | 2003-02-25 | Home Diagnostics, Inc. | Method of strip insertion detection |
| US6541266B2 (en) | 2001-02-28 | 2003-04-01 | Home Diagnostics, Inc. | Method for determining concentration of an analyte in a test strip |
| US6562625B2 (en) | 2001-02-28 | 2003-05-13 | Home Diagnostics, Inc. | Distinguishing test types through spectral analysis |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62232555A (ja) * | 1986-04-02 | 1987-10-13 | Unitika Ltd | 酵素センサ |
-
1951
- 1951-01-28 DE DE19511598067 patent/DE1598067A1/de active Granted
-
1966
- 1966-08-10 US US571416A patent/US3509025A/en not_active Expired - Lifetime
- 1966-08-15 NO NO164305A patent/NO117818B/no unknown
- 1966-08-15 CH CH1171766A patent/CH488186A/de not_active IP Right Cessation
- 1966-08-15 GB GB36385/66A patent/GB1108770A/en not_active Expired
- 1966-08-16 JP JP41053872A patent/JPS503674B1/ja active Pending
- 1966-08-16 BE BE685538D patent/BE685538A/xx unknown
- 1966-08-16 SE SE11081/66A patent/SE337492B/xx unknown
- 1966-08-17 NL NL6611550A patent/NL6611550A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0043181A1 (en) * | 1980-05-26 | 1982-01-06 | Unitika Ltd. | Measuring composition containing enzymes |
| US4438199A (en) | 1980-05-26 | 1984-03-20 | Mitsubishi Petrochemical Co., Ltd. | Measuring composition |
| EP0119722A3 (en) * | 1983-02-16 | 1986-03-05 | Unitika Ltd. | Measuring composition |
| US20030054427A1 (en) * | 1986-08-13 | 2003-03-20 | Roger Phillips | Minimum procedure system for the determination of analytes |
| US6821483B2 (en) | 1986-08-13 | 2004-11-23 | Lifescan, Inc. | Reagents test strip with alignment notch |
| US5843692A (en) * | 1986-08-13 | 1998-12-01 | Lifescan, Inc. | Automatic initiation of a time interval for measuring glucose concentration in a sample of whole blood |
| US6268162B1 (en) | 1986-08-13 | 2001-07-31 | Lifescan, Inc. | Reflectance measurement of analyte concentration with automatic initiation of timing |
| US6887426B2 (en) | 1986-08-13 | 2005-05-03 | Roger Phillips | Reagents test strip adapted for receiving an unmeasured sample while in use in an apparatus |
| US6881550B2 (en) | 1986-08-13 | 2005-04-19 | Roger Phillips | Method for the determination of glucose employing an apparatus emplaced matrix |
| US6858401B2 (en) | 1986-08-13 | 2005-02-22 | Lifescan, Inc. | Minimum procedure system for the determination of analytes |
| US5426032A (en) * | 1986-08-13 | 1995-06-20 | Lifescan, Inc. | No-wipe whole blood glucose test strip |
| US5563042A (en) * | 1986-08-13 | 1996-10-08 | Lifescan, Inc. | Whole blood glucose test strip |
| US20030073152A1 (en) * | 1986-08-13 | 2003-04-17 | Roger Phillips | Minimum procedure system for the determination of analytes |
| US20030073151A1 (en) * | 1986-08-13 | 2003-04-17 | Roger Phillips | Minimum procedure system |
| US20030073153A1 (en) * | 1986-08-13 | 2003-04-17 | Roger Phillips | Minimum procedure system for the determination of analytes |
| US6458326B1 (en) | 1999-11-24 | 2002-10-01 | Home Diagnostics, Inc. | Protective test strip platform |
| US6979571B2 (en) | 1999-11-24 | 2005-12-27 | Home Diagnostics, Inc. | Method of using a protective test strip platform for optical meter apparatus |
| WO2002064819A1 (en) * | 2001-02-14 | 2002-08-22 | International Reagents Corporation | Novel assay method |
| US6562625B2 (en) | 2001-02-28 | 2003-05-13 | Home Diagnostics, Inc. | Distinguishing test types through spectral analysis |
| US6541266B2 (en) | 2001-02-28 | 2003-04-01 | Home Diagnostics, Inc. | Method for determining concentration of an analyte in a test strip |
| US6525330B2 (en) | 2001-02-28 | 2003-02-25 | Home Diagnostics, Inc. | Method of strip insertion detection |
| US7390665B2 (en) | 2001-02-28 | 2008-06-24 | Gilmour Steven B | Distinguishing test types through spectral analysis |
Also Published As
| Publication number | Publication date |
|---|---|
| NO117818B (en, 2012) | 1969-09-29 |
| NL6611550A (en, 2012) | 1967-02-20 |
| DE1598067B2 (en, 2012) | 1973-09-27 |
| DE1598067A1 (de) | 1970-03-26 |
| DE1598067C3 (en, 2012) | 1974-04-18 |
| SE337492B (en, 2012) | 1971-08-09 |
| BE685538A (en, 2012) | 1967-02-16 |
| CH488186A (de) | 1970-03-31 |
| GB1108770A (en) | 1968-04-03 |
| JPS503674B1 (en, 2012) | 1975-02-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Cardini et al. | Enzymic phosphorylation of galactosamine and galactose | |
| Slater | Spectrophotometric determination of fructose-1: 6-diphosphate, hexosemonophosphates, adenosinetriphosphate and adenosinediphosphate | |
| Slein | D-Glucose: Determination with hexokinase and glucose-6-phosphate dehydrogenase | |
| CA1125151A (en) | Triglycerides assay and reagents therefor | |
| Navon et al. | 31P nuclear magnetic resonance studies of Ehrlich ascites tumor cells. | |
| Tsai | Use of phosphorus-31 nuclear magnetic resonance to distinguish bridge and nonbridge oxygens of oxygen-17-enriched nucleoside triphosphates. Stereochemistry of acetate activation by acetyl coenzyme A synthetase | |
| US3509025A (en) | Method and agent for the enzymatic determination of glucose | |
| GB1512328A (en) | Method and reagent for determining the activity of creatinekinase-mb | |
| McComb et al. | Metabolism of ascites tumor cells: III. Effect of 2-deoxyglucose phosphorylation on phosphorus metabolism | |
| US4071413A (en) | Method for determining free fatty acids in blood serum using fatty acid activating enzymes | |
| US4019961A (en) | Analytical enzymatic determination | |
| US4001089A (en) | Method for determination of triglycerides and glycerol | |
| Kaplan | [14] Enzymatic determination of free sugars | |
| Cohn | Some mechanisms of cleavage of adenosine triphosphate and 1, 3-diphosphoglyceric acid | |
| Newbold et al. | Post‐mortem glycolysis in ox skeletal muscle: Effects of mincing and of dilution with or without addition of orthophosphate | |
| Eyer et al. | Synthesis of Glucose 1, 6‐Bisphosphate by the Action of Crystalline Rabbit Muscle Phosphofructokinase | |
| Pontis et al. | Measurement of UDP‐Enzyme Systems | |
| von der Haar et al. | Substrate Properties of Yeast tRNAPhe Oxidized and Reduced at the 3′‐Terminal Ribose | |
| Cunningham et al. | Distances between structural metal ion, substrates, and allosteric modifier of fructose bisphosphatase | |
| Wurster et al. | Anomeric Specificity and Anomerase Activity of Glucosephosphate Isomerase (EC 5.3. 1.9) from Baker’s Yeast | |
| Leloir et al. | [35] Galactokinase and galactowaldenase | |
| Connolly et al. | Direct mass spectroscopic method for determination of oxygen isotope position in adenosine 5'-0-(1-thiotriphosphate). Determination of the stereochemical course of the yeast phenylalanyl-tRNA synthetase reaction | |
| EBATA et al. | THE ENZYMATIC PHOSPHORYLATION OF SEDO-HEPTULOSE | |
| US4151043A (en) | Enzyme determination method | |
| US5250416A (en) | Method for highly sensitive determination of NADH using kinase |