SE453400B

SE453400B - Forfarande for framstellning av fosfonsyraderivat genom odling av en stam horande till streptomyces rubellomurinus, streptomyces rubellomurinus subsp. indigoferus eller streptomyces lavendulae

Forfarande for framstellning av fosfonsyraderivat genom odling av en stam horande till streptomyces rubellomurinus, streptomyces rubellomurinus subsp. indigoferus eller streptomyces lavendulae

Info

Publication number: SE453400B
Authority: SE; Sweden
Prior art keywords: give; acid; reduced pressure; solution; mixture
Prior art date: 1976-07-27

Application number

SE8300288A

Other languages

English (en)

Swedish (sv)

Other versions

SE8300288L (sv

SE8300288D0 (sv

Inventor

Y Kuroda

M Okuhara

E Iguchi

H Aoki

H Imanaka

Original Assignee

Fujisawa Pharmaceutical Co

Priority date

1976-07-27

Filing date

1983-01-20

Publication date

1988-02-01

1983-01-20 Application filed by Fujisawa Pharmaceutical Co filed Critical Fujisawa Pharmaceutical Co

1983-01-20 Publication of SE8300288L publication Critical patent/SE8300288L/sv

1983-01-20 Publication of SE8300288D0 publication Critical patent/SE8300288D0/xx

1988-02-01 Publication of SE453400B publication Critical patent/SE453400B/sv

Links

238000000034 method Methods 0.000 title claims description 105
238000002360 preparation method Methods 0.000 title claims description 47
241001133128 Streptomyces rubellomurinus Species 0.000 title claims description 17
241000187389 Streptomyces lavendulae Species 0.000 title claims description 14
150000003007 phosphonic acid derivatives Chemical class 0.000 title claims description 9
229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 title description 6
-1 2-hydroxytrimethylene Chemical group 0.000 claims description 147
150000003839 salts Chemical class 0.000 claims description 84
230000008569 process Effects 0.000 claims description 73
PKMNDDZSIHLLLI-UHFFFAOYSA-N FR900098 Natural products CC(=O)N(O)CCCP(O)(O)=O PKMNDDZSIHLLLI-UHFFFAOYSA-N 0.000 claims description 46
230000003115 biocidal effect Effects 0.000 claims description 42
241000164932 Streptomyces rubellomurinus subsp. indigoferus Species 0.000 claims description 14
GJXWDTUCERCKIX-UHFFFAOYSA-N fosmidomycin Chemical compound O=CN(O)CCCP(O)(O)=O GJXWDTUCERCKIX-UHFFFAOYSA-N 0.000 claims description 12
235000015097 nutrients Nutrition 0.000 claims description 11
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
YTTBDWKRMPYBDN-HNQUOIGGSA-N [(e)-3-[formyl(hydroxy)amino]prop-1-enyl]phosphonic acid Chemical compound O=CN(O)C\C=C\P(O)(O)=O YTTBDWKRMPYBDN-HNQUOIGGSA-N 0.000 claims description 7
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 7
SMXUDUOWTDBXDT-UHFFFAOYSA-N [3-[acetyl(hydroxy)amino]-2-hydroxypropyl]phosphonic acid Chemical compound CC(=O)N(O)CC(O)CP(O)(O)=O SMXUDUOWTDBXDT-UHFFFAOYSA-N 0.000 claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 326
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 291
239000000203 mixture Substances 0.000 description 272
230000002829 reductive effect Effects 0.000 description 263
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 261
239000000243 solution Substances 0.000 description 256
150000001875 compounds Chemical class 0.000 description 229
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 211
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 186
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 148
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 146
238000003756 stirring Methods 0.000 description 116
238000006243 chemical reaction Methods 0.000 description 99
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 96
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 95
239000007864 aqueous solution Substances 0.000 description 93
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 91
239000011541 reaction mixture Substances 0.000 description 85
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 82
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 79
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 78
238000001816 cooling Methods 0.000 description 77
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 76
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 66
239000013078 crystal Substances 0.000 description 58
238000001914 filtration Methods 0.000 description 58
238000002329 infrared spectrum Methods 0.000 description 58
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 57
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 56
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 55
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 51
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 51
239000002253 acid Substances 0.000 description 49
238000001228 spectrum Methods 0.000 description 49
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 46
239000000706 filtrate Substances 0.000 description 43
239000002904 solvent Substances 0.000 description 42
239000007858 starting material Substances 0.000 description 42
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 41
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 40
239000000126 substance Substances 0.000 description 39
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 38
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 38
239000007788 liquid Substances 0.000 description 38
229910052943 magnesium sulfate Inorganic materials 0.000 description 38
235000019341 magnesium sulphate Nutrition 0.000 description 38
125000002252 acyl group Chemical group 0.000 description 36
239000003795 chemical substances by application Substances 0.000 description 36
239000012071 phase Substances 0.000 description 36
NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 34
238000010992 reflux Methods 0.000 description 32
238000004440 column chromatography Methods 0.000 description 31
239000003921 oil Substances 0.000 description 31
235000019198 oils Nutrition 0.000 description 31
230000007062 hydrolysis Effects 0.000 description 30
238000006460 hydrolysis reaction Methods 0.000 description 30
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 28
150000002148 esters Chemical class 0.000 description 28
235000019253 formic acid Nutrition 0.000 description 28
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
239000000843 powder Substances 0.000 description 27
239000011780 sodium chloride Substances 0.000 description 26
229920001817 Agar Polymers 0.000 description 25
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
239000008272 agar Substances 0.000 description 25
239000002244 precipitate Substances 0.000 description 25
238000000855 fermentation Methods 0.000 description 23
230000004151 fermentation Effects 0.000 description 23
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 23
CRZNAZZXMBDMBS-UHFFFAOYSA-N 3-(hydroxyamino)propylphosphonic acid Chemical compound ONCCCP(O)(O)=O CRZNAZZXMBDMBS-UHFFFAOYSA-N 0.000 description 22
125000000217 alkyl group Chemical group 0.000 description 22
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
230000015572 biosynthetic process Effects 0.000 description 20
238000001704 evaporation Methods 0.000 description 20
239000002609 medium Substances 0.000 description 20
150000007524 organic acids Chemical class 0.000 description 20
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
229920006395 saturated elastomer Polymers 0.000 description 20
229910052783 alkali metal Inorganic materials 0.000 description 19
239000008346 aqueous phase Substances 0.000 description 19
229910002027 silica gel Inorganic materials 0.000 description 19
239000000741 silica gel Substances 0.000 description 19
229910000030 sodium bicarbonate Inorganic materials 0.000 description 19
235000017557 sodium bicarbonate Nutrition 0.000 description 19
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 18
150000007529 inorganic bases Chemical class 0.000 description 18
150000007530 organic bases Chemical class 0.000 description 18
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 17
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
235000011114 ammonium hydroxide Nutrition 0.000 description 17
239000003242 anti bacterial agent Substances 0.000 description 17
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
125000004432 carbon atom Chemical group C* 0.000 description 16
239000000725 suspension Substances 0.000 description 16
238000005406 washing Methods 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
238000000862 absorption spectrum Methods 0.000 description 15
238000010908 decantation Methods 0.000 description 15
238000000354 decomposition reaction Methods 0.000 description 15
230000008020 evaporation Effects 0.000 description 15
238000010438 heat treatment Methods 0.000 description 15
150000001340 alkali metals Chemical class 0.000 description 14
239000001913 cellulose Substances 0.000 description 14
229920002678 cellulose Polymers 0.000 description 14
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 14
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 13
125000002947 alkylene group Chemical group 0.000 description 13
229940088710 antibiotic agent Drugs 0.000 description 13
239000002585 base Substances 0.000 description 13
239000000284 extract Substances 0.000 description 13
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 13
229910000104 sodium hydride Inorganic materials 0.000 description 13
239000012312 sodium hydride Substances 0.000 description 13
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
244000005700 microbiome Species 0.000 description 12
239000011734 sodium Substances 0.000 description 12
229910052708 sodium Inorganic materials 0.000 description 12
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 12
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 12
229910052739 hydrogen Inorganic materials 0.000 description 11
239000002198 insoluble material Substances 0.000 description 11
239000002480 mineral oil Substances 0.000 description 11
125000001424 substituent group Chemical group 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
229910052784 alkaline earth metal Inorganic materials 0.000 description 10
239000003957 anion exchange resin Substances 0.000 description 10
239000006185 dispersion Substances 0.000 description 10
238000010828 elution Methods 0.000 description 10
229910052736 halogen Inorganic materials 0.000 description 10
150000002367 halogens Chemical class 0.000 description 10
239000001257 hydrogen Substances 0.000 description 10
238000004519 manufacturing process Methods 0.000 description 10
229940042472 mineral oil Drugs 0.000 description 10
235000010446 mineral oil Nutrition 0.000 description 10
239000003208 petroleum Substances 0.000 description 10
238000011282 treatment Methods 0.000 description 10
229920002472 Starch Polymers 0.000 description 9
241000187747 Streptomyces Species 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 9
IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 9
239000007795 chemical reaction product Substances 0.000 description 9
239000003480 eluent Substances 0.000 description 9
150000007522 mineralic acids Chemical class 0.000 description 9
239000007787 solid Substances 0.000 description 9
239000008107 starch Substances 0.000 description 9
235000019698 starch Nutrition 0.000 description 9
YNRAFGRKFVERMD-UHFFFAOYSA-N (ethoxycarbonylamino) ethyl carbonate Chemical compound CCOC(=O)NOC(=O)OCC YNRAFGRKFVERMD-UHFFFAOYSA-N 0.000 description 8
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 8
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 8
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 8
238000001103 continuous-wave nuclear magnetic resonance spectrum Methods 0.000 description 8
239000000463 material Substances 0.000 description 8
239000012452 mother liquor Substances 0.000 description 8
125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 8
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 7
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 7
SMXUDUOWTDBXDT-RXMQYKEDSA-N [(2r)-3-[acetyl(hydroxy)amino]-2-hydroxypropyl]phosphonic acid Chemical compound CC(=O)N(O)C[C@@H](O)CP(O)(O)=O SMXUDUOWTDBXDT-RXMQYKEDSA-N 0.000 description 7
150000001335 aliphatic alkanes Chemical group 0.000 description 7
125000005907 alkyl ester group Chemical group 0.000 description 7
125000003118 aryl group Chemical group 0.000 description 7
239000012141 concentrate Substances 0.000 description 7
238000002955 isolation Methods 0.000 description 7
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 7
229910021653 sulphate ion Inorganic materials 0.000 description 7
BGLAMXJBTZOWLK-UHFFFAOYSA-N 3-[[4-acetyl-2,3,6-trihydroxy-5-(3-methylbut-2-enyl)phenyl]methyl]-4-hydroxy-5,6-dimethylpyran-2-one Chemical compound OC1=C(C(C)=O)C(CC=C(C)C)=C(O)C(CC=2C(OC(C)=C(C)C=2O)=O)=C1O BGLAMXJBTZOWLK-UHFFFAOYSA-N 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 6
241000699666 Mus <mouse, genus> Species 0.000 description 6
230000006181 N-acylation Effects 0.000 description 6
240000004808 Saccharomyces cerevisiae Species 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
229930006000 Sucrose Natural products 0.000 description 6
238000005917 acylation reaction Methods 0.000 description 6
150000001342 alkaline earth metals Chemical class 0.000 description 6
125000004450 alkenylene group Chemical group 0.000 description 6
238000010171 animal model Methods 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
229920001429 chelating resin Polymers 0.000 description 6
238000005345 coagulation Methods 0.000 description 6
230000015271 coagulation Effects 0.000 description 6
238000000605 extraction Methods 0.000 description 6
239000000499 gel Substances 0.000 description 6
239000008273 gelatin Substances 0.000 description 6
229920000159 gelatin Polymers 0.000 description 6
125000000623 heterocyclic group Chemical group 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
230000002906 microbiologic effect Effects 0.000 description 6
230000000877 morphologic effect Effects 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
159000000000 sodium salts Chemical class 0.000 description 6
241000894007 species Species 0.000 description 6
239000005720 sucrose Substances 0.000 description 6
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
241000699670 Mus sp. Species 0.000 description 5
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 5
150000008065 acid anhydrides Chemical class 0.000 description 5
125000001931 aliphatic group Chemical group 0.000 description 5
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