JPS6188888A

JPS6188888A - 酵素法有機リン酸エステル誘導体の製法

酵素法有機リン酸エステル誘導体の製法

Info

Publication number: JPS6188888A
Authority: JP; Japan
Prior art keywords: group; ring; phosphorylcholine; residue; propanol
Prior art date: 1984-10-08
Legal status : Granted

Application number

JP20993384A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0571236B2 (enrdf_load_stackoverflow

Inventor

Sumitaka Kokusho

国生　純孝

Mineo Nakayama

中山　峯雄

Akira Tsunoda

昭角田

Shigeaki Kato

重昭加藤

Haruo Machida

晴夫町田

Shinjiro Iwasaki

岩崎　慎二郎

Current Assignee

Meito Sangyo KK

Original Assignee

Meito Sangyo KK

Priority date

1984-10-08

Filing date

1984-10-08

Publication date

1986-05-07

1984-10-08 Application filed by Meito Sangyo KK filed Critical Meito Sangyo KK

1984-10-08 Priority to JP20993384A priority Critical patent/JPS6188888A/ja

1986-05-07 Publication of JPS6188888A publication Critical patent/JPS6188888A/ja

1993-10-06 Publication of JPH0571236B2 publication Critical patent/JPH0571236B2/ja

Status Granted legal-status Critical Current

Links

150000003014 phosphoric acid esters Chemical class 0.000 title claims abstract description 21
238000000034 method Methods 0.000 title abstract description 36
230000002255 enzymatic effect Effects 0.000 title abstract description 5
238000002360 preparation method Methods 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 46
230000001476 alcoholic effect Effects 0.000 claims abstract description 32
ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 claims abstract description 28
102000015439 Phospholipases Human genes 0.000 claims abstract description 28
108010064785 Phospholipases Proteins 0.000 claims abstract description 28
238000004519 manufacturing process Methods 0.000 claims abstract description 15
-1 pregnane steroid compound Chemical group 0.000 claims description 194
125000001424 substituent group Chemical group 0.000 claims description 78
125000003277 amino group Chemical group 0.000 claims description 37
229920006395 saturated elastomer Polymers 0.000 claims description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 33
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
229910052736 halogen Inorganic materials 0.000 claims description 32
150000002367 halogens Chemical class 0.000 claims description 32
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
125000000217 alkyl group Chemical group 0.000 claims description 26
125000002252 acyl group Chemical group 0.000 claims description 23
125000003118 aryl group Chemical group 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
125000003545 alkoxy group Chemical group 0.000 claims description 18
125000000623 heterocyclic group Chemical group 0.000 claims description 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
150000001338 aliphatic hydrocarbons Chemical group 0.000 claims description 15
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
125000004414 alkyl thio group Chemical group 0.000 claims description 13
239000000126 substance Substances 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 12
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 11
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
125000002947 alkylene group Chemical group 0.000 claims description 11
125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
235000000346 sugar Nutrition 0.000 claims description 11
125000003396 thiol group Chemical group [H]S* 0.000 claims description 11
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
125000004193 piperazinyl group Chemical group 0.000 claims description 10
125000003386 piperidinyl group Chemical group 0.000 claims description 9
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 8
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
125000004043 oxo group Chemical group O=* 0.000 claims description 8
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
125000005543 phthalimide group Chemical group 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
150000002430 hydrocarbons Chemical group 0.000 claims description 6
125000002560 nitrile group Chemical group 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
GIIGHSIIKVOWKZ-UHFFFAOYSA-N 2h-triazolo[4,5-d]pyrimidine Chemical group N1=CN=CC2=NNN=C21 GIIGHSIIKVOWKZ-UHFFFAOYSA-N 0.000 claims description 5
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 5
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 5
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical group OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 4
ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical group C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims description 4
SHZGCJCMOBCMKK-UHFFFAOYSA-N 6-methyloxane-2,3,4,5-tetrol Chemical group CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 4
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 4
125000002632 imidazolidinyl group Chemical group 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
125000002971 oxazolyl group Chemical group 0.000 claims description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
125000000542 sulfonic acid group Chemical group 0.000 claims description 4
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 3
HNXQXTQTPAJEJL-UHFFFAOYSA-N 2-aminopteridin-4-ol Chemical group C1=CN=C2NC(N)=NC(=O)C2=N1 HNXQXTQTPAJEJL-UHFFFAOYSA-N 0.000 claims description 3
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 3
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 3
150000001924 cycloalkanes Chemical group 0.000 claims description 3
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
125000001041 indolyl group Chemical group 0.000 claims description 3
125000006501 nitrophenyl group Chemical group 0.000 claims description 3
AHKZTVQIVOEVFO-UHFFFAOYSA-N oxide(2-) Chemical compound [O-2] AHKZTVQIVOEVFO-UHFFFAOYSA-N 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical group C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 2
YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical group C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims description 2
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 3
229910052760 oxygen Inorganic materials 0.000 claims 2
SPAMRUYRVYMHPV-UHFFFAOYSA-N 3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical group C1=CCCC2C(=O)NC(=O)C21 SPAMRUYRVYMHPV-UHFFFAOYSA-N 0.000 claims 1
XZLIYCQRASOFQM-UHFFFAOYSA-N 5h-imidazo[4,5-d]triazine Chemical group N1=NC=C2NC=NC2=N1 XZLIYCQRASOFQM-UHFFFAOYSA-N 0.000 claims 1
125000000600 disaccharide group Chemical group 0.000 claims 1
125000002017 heptosyl group Chemical group 0.000 claims 1
125000000625 hexosyl group Chemical group 0.000 claims 1
102000005962 receptors Human genes 0.000 abstract description 18
108020003175 receptors Proteins 0.000 abstract description 18
238000006911 enzymatic reaction Methods 0.000 abstract description 5
239000006227 byproduct Substances 0.000 abstract 1
238000010189 synthetic method Methods 0.000 abstract 1
229950004354 phosphorylcholine Drugs 0.000 description 273
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 100
239000000758 substrate Substances 0.000 description 60
125000001931 aliphatic group Chemical group 0.000 description 41
238000006243 chemical reaction Methods 0.000 description 40
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 40
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 38
239000000243 solution Substances 0.000 description 38
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 34
239000002253 acid Substances 0.000 description 30
NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 28
102000011420 Phospholipase D Human genes 0.000 description 26
108090000553 Phospholipase D Proteins 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
229910019142 PO4 Inorganic materials 0.000 description 23
235000021317 phosphate Nutrition 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
239000010452 phosphate Substances 0.000 description 22
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
238000003756 stirring Methods 0.000 description 20
150000002148 esters Chemical class 0.000 description 19
239000007858 starting material Substances 0.000 description 19
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 18
150000001298 alcohols Chemical class 0.000 description 18
229910052698 phosphorus Inorganic materials 0.000 description 18
239000011574 phosphorus Substances 0.000 description 18
239000000047 product Substances 0.000 description 17
239000002904 solvent Substances 0.000 description 17
PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 16
239000000203 mixture Substances 0.000 description 16
239000007864 aqueous solution Substances 0.000 description 15
229960001231 choline Drugs 0.000 description 15
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
230000000694 effects Effects 0.000 description 15
229910000147 aluminium phosphate Inorganic materials 0.000 description 14
239000003153 chemical reaction reagent Substances 0.000 description 13
150000003904 phospholipids Chemical class 0.000 description 13
150000004945 aromatic hydrocarbons Chemical group 0.000 description 12
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 12
150000002402 hexoses Chemical group 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 10
239000000787 lecithin Substances 0.000 description 10
229940067606 lecithin Drugs 0.000 description 10
235000010445 lecithin Nutrition 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
230000009471 action Effects 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
239000012141 concentrate Substances 0.000 description 8
BJRNKVDFDLYUGJ-RMPHRYRLSA-N hydroquinone O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 description 8
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 8
235000012239 silicon dioxide Nutrition 0.000 description 8
240000007124 Brassica oleracea Species 0.000 description 7
235000003899 Brassica oleracea var acephala Nutrition 0.000 description 7
235000011301 Brassica oleracea var capitata Nutrition 0.000 description 7
235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 7
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 7
102000004190 Enzymes Human genes 0.000 description 7
108090000790 Enzymes Proteins 0.000 description 7
241000203622 Nocardiopsis Species 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
238000012546 transfer Methods 0.000 description 7
238000006276 transfer reaction Methods 0.000 description 7
SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical group O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 6
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 6
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
150000002972 pentoses Chemical group 0.000 description 6
PYJNAPOPMIJKJZ-UHFFFAOYSA-N phosphorylcholine chloride Chemical compound [Cl-].C[N+](C)(C)CCOP(O)(O)=O PYJNAPOPMIJKJZ-UHFFFAOYSA-N 0.000 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 6
239000002994 raw material Substances 0.000 description 6
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 5
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 description 5
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
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 5
239000001110 calcium chloride Substances 0.000 description 5
229910001628 calcium chloride Inorganic materials 0.000 description 5
239000013078 crystal Substances 0.000 description 5
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
239000008103 glucose Substances 0.000 description 5
235000011187 glycerol Nutrition 0.000 description 5
150000002327 glycerophospholipids Chemical class 0.000 description 5
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
239000008101 lactose Substances 0.000 description 5
239000002609 medium Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
150000008163 sugars Chemical class 0.000 description 5
238000001308 synthesis method Methods 0.000 description 5
241000187362 Actinomadura Species 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
229930006000 Sucrose Natural products 0.000 description 4
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 4
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 4
239000003125 aqueous solvent Substances 0.000 description 4
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 4
229960000271 arbutin Drugs 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 4
239000000872 buffer Substances 0.000 description 4
238000005119 centrifugation Methods 0.000 description 4
239000004020 conductor Substances 0.000 description 4
235000013681 dietary sucrose Nutrition 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
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