NL8620072A - Werkwijze voor de bereiding van n-formyl-l-peptiden. - Google Patents
Werkwijze voor de bereiding van n-formyl-l-peptiden. Download PDFInfo
- Publication number
- NL8620072A NL8620072A NL8620072A NL8620072A NL8620072A NL 8620072 A NL8620072 A NL 8620072A NL 8620072 A NL8620072 A NL 8620072A NL 8620072 A NL8620072 A NL 8620072A NL 8620072 A NL8620072 A NL 8620072A
- Authority
- NL
- Netherlands
- Prior art keywords
- formyl
- ala
- gly
- bacillus
- preparation
- Prior art date
Links
- 150000001413 amino acids Chemical class 0.000 title claims description 35
- 108090000765 processed proteins & peptides Proteins 0.000 title abstract description 36
- 108091005804 Peptidases Proteins 0.000 title description 5
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 title 1
- -1 N-formyl amino Chemical group 0.000 claims abstract description 51
- 108010006035 Metalloproteases Proteins 0.000 claims abstract description 20
- 102000005741 Metalloproteases Human genes 0.000 claims abstract description 20
- DEFJQIDDEAULHB-IMJSIDKUSA-N L-alanyl-L-alanine Chemical compound C[C@H](N)C(=O)N[C@@H](C)C(O)=O DEFJQIDDEAULHB-IMJSIDKUSA-N 0.000 claims abstract description 8
- 108010056243 alanylalanine Proteins 0.000 claims abstract description 8
- CXISPYVYMQWFLE-VKHMYHEASA-N Ala-Gly Chemical compound C[C@H]([NH3+])C(=O)NCC([O-])=O CXISPYVYMQWFLE-VKHMYHEASA-N 0.000 claims abstract description 7
- VPZXBVLAVMBEQI-VKHMYHEASA-N Glycyl-alanine Chemical compound OC(=O)[C@H](C)NC(=O)CN VPZXBVLAVMBEQI-VKHMYHEASA-N 0.000 claims abstract description 7
- 108010079364 N-glycylalanine Proteins 0.000 claims abstract description 7
- 108010047495 alanylglycine Proteins 0.000 claims abstract description 7
- VPZXBVLAVMBEQI-UHFFFAOYSA-N glycyl-DL-alpha-alanine Natural products OC(=O)C(C)NC(=O)CN VPZXBVLAVMBEQI-UHFFFAOYSA-N 0.000 claims abstract description 7
- YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 claims abstract description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 51
- 238000002360 preparation method Methods 0.000 claims description 48
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 20
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 244000005700 microbiome Species 0.000 claims description 12
- 238000009833 condensation Methods 0.000 claims description 11
- 230000005494 condensation Effects 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 9
- 241000193744 Bacillus amyloliquefaciens Species 0.000 claims description 6
- 244000063299 Bacillus subtilis Species 0.000 claims description 5
- 241000193389 Bacillus thermoproteolyticus Species 0.000 claims description 5
- 235000014469 Bacillus subtilis Nutrition 0.000 claims description 4
- 241000194105 Paenibacillus polymyxa Species 0.000 claims description 4
- 241000894007 species Species 0.000 claims description 4
- 150000008575 L-amino acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims 1
- 241000194110 Bacillus sp. (in: Bacteria) Species 0.000 abstract 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 40
- 239000000047 product Substances 0.000 description 39
- 229940024606 amino acid Drugs 0.000 description 34
- 235000001014 amino acid Nutrition 0.000 description 33
- 239000000203 mixture Substances 0.000 description 27
- 102000004190 Enzymes Human genes 0.000 description 26
- 108090000790 Enzymes Proteins 0.000 description 26
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 24
- 229940088598 enzyme Drugs 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 150000004702 methyl esters Chemical class 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- 102000004196 processed proteins & peptides Human genes 0.000 description 20
- 238000005755 formation reaction Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 108090001109 Thermolysin Proteins 0.000 description 17
- 108010011485 Aspartame Proteins 0.000 description 16
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 16
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 15
- 239000000605 aspartame Substances 0.000 description 15
- 229960003438 aspartame Drugs 0.000 description 15
- 235000010357 aspartame Nutrition 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 15
- 229960005190 phenylalanine Drugs 0.000 description 14
- 229960005261 aspartic acid Drugs 0.000 description 13
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 13
- 125000006239 protecting group Chemical group 0.000 description 13
- 235000003704 aspartic acid Nutrition 0.000 description 11
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 11
- 235000008729 phenylalanine Nutrition 0.000 description 11
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- 239000002243 precursor Substances 0.000 description 9
- WYYUBJAMROQJSF-QWRGUYRKSA-N (3s)-4-[[(1s)-1-carboxy-2-phenylethyl]amino]-3-formamido-4-oxobutanoic acid Chemical compound OC(=O)C[C@H](NC=O)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 WYYUBJAMROQJSF-QWRGUYRKSA-N 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- 230000004224 protection Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 7
- NMFZSGJFWAFCAZ-WHFBIAKZSA-N (2S)-2-[[(2S)-2-formamidopropanoyl]amino]propanoic acid Chemical compound C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)O NMFZSGJFWAFCAZ-WHFBIAKZSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- DOALFVREZUXSEB-QRPNPIFTSA-N (2s)-2-amino-3-phenylpropanoic acid;chloromethane Chemical compound ClC.OC(=O)[C@@H](N)CC1=CC=CC=C1 DOALFVREZUXSEB-QRPNPIFTSA-N 0.000 description 5
- AXZJHDNQDSVIDR-NSHDSACASA-N 4178-93-2 Chemical compound CC(C)C[C@H](N)C(=O)NC1=CC=C([N+]([O-])=O)C=C1 AXZJHDNQDSVIDR-NSHDSACASA-N 0.000 description 5
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 5
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 5
- 125000003275 alpha amino acid group Chemical group 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 150000001540 azides Chemical group 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 229960003136 leucine Drugs 0.000 description 5
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- GJHIOWXZFDVUKQ-AWEZNQCLSA-N 2360-97-6 Chemical compound C([C@H](N)C(=O)NC=1C=CC(=CC=1)[N+]([O-])=O)C1=CC=CC=C1 GJHIOWXZFDVUKQ-AWEZNQCLSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 125000000998 L-alanino group Chemical group [H]N([*])[C@](C([H])([H])[H])([H])C(=O)O[H] 0.000 description 4
- PYUSHNKNPOHWEZ-YFKPBYRVSA-N N-formyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC=O PYUSHNKNPOHWEZ-YFKPBYRVSA-N 0.000 description 4
- 102000035195 Peptidases Human genes 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- OSEHTEQTVJQGDE-RYUDHWBXSA-N (3s)-3-formamido-4-[[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid Chemical compound OC(=O)C[C@H](NC=O)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 OSEHTEQTVJQGDE-RYUDHWBXSA-N 0.000 description 3
- 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 3
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- UGJBHEZMOKVTIM-UHFFFAOYSA-N N-formylglycine Chemical compound OC(=O)CNC=O UGJBHEZMOKVTIM-UHFFFAOYSA-N 0.000 description 3
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000000539 amino acid group Chemical group 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 150000003931 anilides Chemical class 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- 239000011942 biocatalyst Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 238000006911 enzymatic reaction Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000010647 peptide synthesis reaction Methods 0.000 description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 3
- 235000019833 protease Nutrition 0.000 description 3
- 230000006340 racemization Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000012086 standard solution Substances 0.000 description 3
- OXVNHELYAFWNQA-QRPNPIFTSA-N (2S)-2-amino-3-phenylpropanoic acid methyl prop-2-enoate Chemical compound C(C=C)(=O)OC.N[C@@H](CC1=CC=CC=C1)C(=O)O OXVNHELYAFWNQA-QRPNPIFTSA-N 0.000 description 2
- AXZFINGICKCIHO-UHFFFAOYSA-N 2-formamido-n-phenylacetamide Chemical compound O=CNCC(=O)NC1=CC=CC=C1 AXZFINGICKCIHO-UHFFFAOYSA-N 0.000 description 2
- MQUUQXIFCBBFDP-UHFFFAOYSA-N 2-formamidobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)NC=O MQUUQXIFCBBFDP-UHFFFAOYSA-N 0.000 description 2
- SRBATDDRZARFDZ-UHFFFAOYSA-N 2-formamidopropanoic acid Chemical compound OC(=O)C(C)NC=O SRBATDDRZARFDZ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
- 206010057249 Phagocytosis Diseases 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 229920005654 Sephadex Polymers 0.000 description 2
- 239000012507 Sephadex™ Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000004279 alanine Nutrition 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229960004050 aminobenzoic acid Drugs 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 235000011148 calcium chloride Nutrition 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 230000022244 formylation Effects 0.000 description 2
- 238000006170 formylation reaction Methods 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000008782 phagocytosis Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- QTAUYVXANXTPNC-UWVGGRQHSA-N (2s)-2-[[(2s)-2-formamido-4-methylsulfanylbutanoyl]amino]-4-methylpentanoic acid Chemical compound CSCC[C@H](NC=O)C(=O)N[C@@H](CC(C)C)C(O)=O QTAUYVXANXTPNC-UWVGGRQHSA-N 0.000 description 1
- NKFWAXNWEJTXGY-ONGXEEELSA-N (3S)-4-(N-[(1S)-1-carboxyethyl]anilino)-3-formamido-4-oxobutanoic acid Chemical compound C[C@@H](C(=O)O)N(C1=CC=CC=C1)C(=O)[C@H](CC(=O)O)NC=O NKFWAXNWEJTXGY-ONGXEEELSA-N 0.000 description 1
- 102000004400 Aminopeptidases Human genes 0.000 description 1
- 108090000915 Aminopeptidases Proteins 0.000 description 1
- 241000304886 Bacilli Species 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 108010001857 Cell Surface Receptors Proteins 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- DOALFVREZUXSEB-UHFFFAOYSA-N ClC.OC(=O)C(N)CC1=CC=CC=C1 Chemical compound ClC.OC(=O)C(N)CC1=CC=CC=C1 DOALFVREZUXSEB-UHFFFAOYSA-N 0.000 description 1
- 108010016626 Dipeptides Proteins 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- 108010008211 N-Formylmethionine Leucyl-Phenylalanine Proteins 0.000 description 1
- MQUUQXIFCBBFDP-VKHMYHEASA-N N-formyl-L-aspartic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC=O MQUUQXIFCBBFDP-VKHMYHEASA-N 0.000 description 1
- NSTPXGARCQOSAU-VIFPVBQESA-N N-formyl-L-phenylalanine Chemical compound O=CN[C@H](C(=O)O)CC1=CC=CC=C1 NSTPXGARCQOSAU-VIFPVBQESA-N 0.000 description 1
- 125000001429 N-terminal alpha-amino-acid group Chemical group 0.000 description 1
- 102100029251 Phagocytosis-stimulating peptide Human genes 0.000 description 1
- 101710177686 Phagocytosis-stimulating peptide Proteins 0.000 description 1
- 241000132152 Polymyxa Species 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 102000012479 Serine Proteases Human genes 0.000 description 1
- 108010022999 Serine Proteases Proteins 0.000 description 1
- 101000693530 Staphylococcus aureus Staphylokinase Proteins 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 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 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- MTEUMURLJRZUKD-UHFFFAOYSA-N acetic acid;butan-1-ol;pyridine;hydrate Chemical compound O.CC(O)=O.CCCCO.C1=CC=NC=C1 MTEUMURLJRZUKD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- PRQROPMIIGLWRP-BZSNNMDCSA-N chemotactic peptide Chemical compound CSCC[C@H](NC=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 PRQROPMIIGLWRP-BZSNNMDCSA-N 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 208000002925 dental caries Diseases 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- VGGRCVDNFAQIKO-UHFFFAOYSA-N formic anhydride Chemical compound O=COC=O VGGRCVDNFAQIKO-UHFFFAOYSA-N 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- 230000033001 locomotion Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 102000006240 membrane receptors Human genes 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 150000002741 methionine derivatives Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000019520 non-alcoholic beverage Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 210000001539 phagocyte Anatomy 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000009979 protective mechanism Effects 0.000 description 1
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- 230000029305 taxis Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/0606—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing heteroatoms not provided for by C07K5/06086 - C07K5/06139, e.g. Ser, Met, Cys, Thr
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P21/00—Preparation of peptides or proteins
- C12P21/02—Preparation of peptides or proteins having a known sequence of two or more amino acids, e.g. glutathione
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Biophysics (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU3855631 | 1985-02-15 | ||
| SU3855631 | 1985-02-15 | ||
| SU4014768 | 1986-02-10 | ||
| SU4014768 | 1986-02-10 | ||
| PCT/SU1986/000010 WO1986004924A1 (en) | 1985-02-15 | 1986-02-13 | Method of obtaining n-formyl-l peptides |
| SU8600010 | 1986-02-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8620072A true NL8620072A (nl) | 1986-12-01 |
Family
ID=26666020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8620072A NL8620072A (nl) | 1985-02-15 | 1986-02-13 | Werkwijze voor de bereiding van n-formyl-l-peptiden. |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE3690076T1 (enrdf_load_stackoverflow) |
| NL (1) | NL8620072A (enrdf_load_stackoverflow) |
| WO (1) | WO1986004924A1 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0272564B1 (en) * | 1986-12-22 | 1993-10-20 | Hampshire Chemical Corporation | Enzyme mediated coupling reactions |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5837483A (en) * | 1996-10-15 | 1998-11-17 | Holland Sweetener Company V.O.F. | Enzymatic method for producing N-formyl-α-L-aspartyl-L-phenylalanine methyl ester |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4116768A (en) * | 1975-04-29 | 1978-09-26 | (Zaidanhojin) Sagami Chemical Research Center | Process for producing a peptide |
| US4119493A (en) * | 1975-10-23 | 1978-10-10 | (Zaidanhojin) Sagami Chemical Research Center | Process for producing a peptide |
| JPS55135595A (en) * | 1979-04-03 | 1980-10-22 | Toyo Soda Mfg Co Ltd | Preparation of dipeptide |
| US4293648A (en) * | 1979-12-12 | 1981-10-06 | G. D. Searle & Co. | Process for esterification of α-L-aspartyl-L-phenylalanine |
| JPS57146595A (en) * | 1981-02-02 | 1982-09-10 | Searle & Co | Production of amino protected-l- aspartyl-l-phenylalanine alkyl ester |
| JPS60164495A (ja) * | 1984-01-16 | 1985-08-27 | モンサント コンパニー | Ｎ‐ホルミルアミノ酸とペプチド残基の酵素的結合法 |
-
1986
- 1986-02-13 WO PCT/SU1986/000010 patent/WO1986004924A1/ru unknown
- 1986-02-13 NL NL8620072A patent/NL8620072A/nl unknown
- 1986-02-13 DE DE19863690076 patent/DE3690076T1/de not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0272564B1 (en) * | 1986-12-22 | 1993-10-20 | Hampshire Chemical Corporation | Enzyme mediated coupling reactions |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3690076T1 (enrdf_load_stackoverflow) | 1987-03-12 |
| WO1986004924A1 (en) | 1986-08-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4256836A (en) | Addition compound of dipeptide derivative and amino acid derivative | |
| US4119493A (en) | Process for producing a peptide | |
| US4116768A (en) | Process for producing a peptide | |
| JPH04149166A (ja) | 新規ケト酸アミド誘導体 | |
| CA1059051A (en) | Process for producing a peptide | |
| EP0144103B1 (en) | Methods and compositions for preparation of H-ARG-X-Z-Y-TYR-R | |
| JPH05331072A (ja) | プロリルエンドペプチダーゼ阻害剤 | |
| EP0149594A2 (en) | Enzymatic coupling of n-formyl amino acids and/or peptide residues | |
| Briggs et al. | Polypeptides. Part 17. Aminoxy-analogues of aspartame and gastrin C-terminal tetrapeptide amide | |
| EP1140795B1 (en) | N-3, 3-dimethylbutyl-l-aspartic acid and esters thereof, the process of preparing the same, and the process for preparing n-[n-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanine-1-methylester therefrom | |
| FR2471411A1 (fr) | Nouveaux substrats a-hydroxytripeptidiques utiles notamment comme reactifs pour la determination d'enzymes proteolytiques | |
| NL8620072A (nl) | Werkwijze voor de bereiding van n-formyl-l-peptiden. | |
| US5002872A (en) | Enzyme mediated coupling reactions | |
| Wiggans et al. | Action of cathepsin C on dipeptide esters | |
| US4369137A (en) | N-Protected pentapeptides useful as intermediates in the preparation of thymopoietin pentapeptide | |
| DE68923625T2 (de) | Enzymatischer Prozess zur Herstellung immunomodulatorischer Pentapeptide und Intermediate zu deren Herstellung. | |
| Makowski et al. | Synthesis of Tetrapeptide p‐nitrophenylanilides containing dehydroalanine and dehydrophenylalanine and their influence on cathepsin C activity | |
| US5776903A (en) | Peptide derivatives usable as zinc endopeptidase 24-15 inhibitors | |
| Harnois-Pontoni et al. | Hydrosoluble fluorogenic substrates for plasmin | |
| EP0356595A1 (en) | Novel peptidase inhibitors | |
| FR2499098A1 (fr) | Procede pour la production d'un ester d'alkyle de (l-aspartyl amino-protege)-l-phenylalanine | |
| EP0272564B1 (en) | Enzyme mediated coupling reactions | |
| JP3828214B2 (ja) | ペプチドおよびその塩 | |
| Ohno et al. | Partial enzymic deprotection in the synthesis of a protected octapeptide bearing a free terminal carboxyl group | |
| US4784988A (en) | Peptides correlated to lysozyme |