IE52242B1 - Preparation of amino protected-l-aspartyl-l-phenylalanine alkyl ester - Google Patents
Preparation of amino protected-l-aspartyl-l-phenylalanine alkyl esterInfo
- Publication number
- IE52242B1 IE52242B1 IE220/82A IE22082A IE52242B1 IE 52242 B1 IE52242 B1 IE 52242B1 IE 220/82 A IE220/82 A IE 220/82A IE 22082 A IE22082 A IE 22082A IE 52242 B1 IE52242 B1 IE 52242B1
- Authority
- IE
- Ireland
- Prior art keywords
- amino
- phenylalanine
- alkyl ester
- protected
- aspartyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 59
- 102000004190 Enzymes Human genes 0.000 claims abstract description 34
- 108090000790 Enzymes Proteins 0.000 claims abstract description 34
- 239000004365 Protease Substances 0.000 claims abstract description 26
- 108091005804 Peptidases Proteins 0.000 claims abstract description 24
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 244000005700 microbiome Species 0.000 claims abstract description 19
- 230000000694 effects Effects 0.000 claims abstract description 18
- 229960005190 phenylalanine Drugs 0.000 claims abstract description 13
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 8
- 230000000813 microbial effect Effects 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 230000008878 coupling Effects 0.000 claims abstract description 6
- 238000010168 coupling process Methods 0.000 claims abstract description 6
- 238000005859 coupling reaction Methods 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 150000004702 methyl esters Chemical class 0.000 claims abstract 2
- -1 amino-protected L-aspartic acid Chemical class 0.000 claims description 9
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-Phenylalanine Natural products OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 6
- 230000002255 enzymatic effect Effects 0.000 claims description 5
- 229960005261 aspartic acid Drugs 0.000 claims description 4
- 241000228212 Aspergillus Species 0.000 claims description 2
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 2
- 241000193755 Bacillus cereus Species 0.000 claims description 2
- 241000187747 Streptomyces Species 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004492 methyl ester group Chemical group 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 abstract description 12
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract description 2
- 229940088598 enzyme Drugs 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000000047 product Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 108090000765 processed proteins & peptides Proteins 0.000 description 14
- 235000019419 proteases Nutrition 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 235000010633 broth Nutrition 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 240000001817 Cereus hexagonus Species 0.000 description 6
- 229940024606 amino acid Drugs 0.000 description 6
- 108010006035 Metalloproteases Proteins 0.000 description 5
- 102000005741 Metalloproteases Human genes 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 102000004196 processed proteins & peptides Human genes 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 150000003839 salts Chemical group 0.000 description 5
- 150000001540 azides Chemical class 0.000 description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000010647 peptide synthesis reaction Methods 0.000 description 4
- 230000006340 racemization Effects 0.000 description 4
- 108090000526 Papain Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001408 amides Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000004899 c-terminal region Anatomy 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XYXYXSKSTZAEJW-VIFPVBQESA-N (2s)-2-(phenylmethoxycarbonylamino)butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 XYXYXSKSTZAEJW-VIFPVBQESA-N 0.000 description 2
- POLGZPYHEPOBFG-NSHDSACASA-N (2s)-2-benzamido-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)C1=CC=CC=C1 POLGZPYHEPOBFG-NSHDSACASA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 108090000317 Chymotrypsin Proteins 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 108010038807 Oligopeptides Proteins 0.000 description 2
- 102000015636 Oligopeptides Human genes 0.000 description 2
- 102000035195 Peptidases Human genes 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000539 amino acid group Chemical group 0.000 description 2
- 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 2
- 238000003556 assay Methods 0.000 description 2
- 229960002376 chymotrypsin Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000002054 inoculum Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229940055729 papain Drugs 0.000 description 2
- 235000019834 papain Nutrition 0.000 description 2
- 229920001184 polypeptide Polymers 0.000 description 2
- 239000011369 resultant mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- ASFAFOSQXBRFMV-LJQANCHMSA-N 3-n-(2-benzyl-1,3-dihydroxypropan-2-yl)-1-n-[(1r)-1-(4-fluorophenyl)ethyl]-5-[methyl(methylsulfonyl)amino]benzene-1,3-dicarboxamide Chemical compound N([C@H](C)C=1C=CC(F)=CC=1)C(=O)C(C=1)=CC(N(C)S(C)(=O)=O)=CC=1C(=O)NC(CO)(CO)CC1=CC=CC=C1 ASFAFOSQXBRFMV-LJQANCHMSA-N 0.000 description 1
- 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 1
- 108700023418 Amidases Proteins 0.000 description 1
- 240000006439 Aspergillus oryzae Species 0.000 description 1
- 235000002247 Aspergillus oryzae Nutrition 0.000 description 1
- 241000193389 Bacillus thermoproteolyticus Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000599985 Beijerinckia mobilis Species 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 1
- 108010016626 Dipeptides Proteins 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 238000010268 HPLC based assay Methods 0.000 description 1
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- KUUUDPTUEOKITK-AWEZNQCLSA-N N-benzoyl-L-tyrosine Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=CC=CC=1)C1=CC=C(O)C=C1 KUUUDPTUEOKITK-AWEZNQCLSA-N 0.000 description 1
- 241000194105 Paenibacillus polymyxa Species 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 241000364057 Peoria Species 0.000 description 1
- 240000009305 Pometia pinnata Species 0.000 description 1
- 235000017284 Pometia pinnata Nutrition 0.000 description 1
- 108010059712 Pronase Proteins 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000187392 Streptomyces griseus Species 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
- 108090001109 Thermolysin Proteins 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 102000005922 amidase Human genes 0.000 description 1
- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000008122 artificial sweetener Substances 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229940111685 dibasic potassium phosphate Drugs 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 229940079919 digestives enzyme preparation Drugs 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 108010007093 dispase Proteins 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000003269 fluorescent indicator Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 229940076230 magnesium sulfate monohydrate Drugs 0.000 description 1
- LFCFXZHKDRJMNS-UHFFFAOYSA-L magnesium;sulfate;hydrate Chemical compound O.[Mg+2].[O-]S([O-])(=O)=O LFCFXZHKDRJMNS-UHFFFAOYSA-L 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- SWVMLNPDTIFDDY-FVGYRXGTSA-N methyl (2s)-2-amino-3-phenylpropanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CC1=CC=CC=C1 SWVMLNPDTIFDDY-FVGYRXGTSA-N 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- RJQRCOMHVBLQIH-UHFFFAOYSA-N pentane-1-sulfonic acid Chemical compound CCCCCS(O)(=O)=O RJQRCOMHVBLQIH-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005891 transamination reaction Methods 0.000 description 1
- 239000001974 tryptic soy broth Substances 0.000 description 1
- 108010050327 trypticase-soy broth Proteins 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 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
- C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
- C07K5/0613—Aspartame
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23056981A | 1981-02-02 | 1981-02-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE820220L IE820220L (en) | 1982-08-02 |
| IE52242B1 true IE52242B1 (en) | 1987-08-19 |
Family
ID=22865706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE220/82A IE52242B1 (en) | 1981-02-02 | 1982-02-01 | Preparation of amino protected-l-aspartyl-l-phenylalanine alkyl ester |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS57146595A (enrdf_load_stackoverflow) |
| DE (1) | DE3203292A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2499098A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2092161B (enrdf_load_stackoverflow) |
| IE (1) | IE52242B1 (enrdf_load_stackoverflow) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5917997A (ja) * | 1982-07-23 | 1984-01-30 | Toyo Soda Mfg Co Ltd | ジペプチドエステルとアミノ酸エステルとの付加化合物の製造方法 |
| EP0124313B1 (en) * | 1983-04-28 | 1989-08-02 | Ajinomoto Co., Inc. | Process for the production of l-aspartyl-l-phenylalanine methyl ester or l-aspartyl-l-phenylalanine |
| 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 |
| GB8403611D0 (en) * | 1984-02-10 | 1984-03-14 | Tate & Lyle Plc | Sweetener |
| DE3690076T1 (enrdf_load_stackoverflow) * | 1985-02-15 | 1987-03-12 | ||
| EP0230649A1 (en) * | 1986-01-02 | 1987-08-05 | Miles Inc. | Immobilization of phenylaline ammonia-lyase |
| WO1987006268A1 (en) * | 1986-04-10 | 1987-10-22 | Commonwealth Scientific And Industrial Research Or | Enzymatic synthesis |
| FR2649121B1 (fr) * | 1989-07-03 | 1991-09-20 | Rhone Poulenc Chimie | Procede de preparation enzymatique de dipeptides comportant un reste derive d'un acide amino-cycloalkyl carboxylique |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3972773A (en) * | 1975-04-29 | 1976-08-03 | Sagami Chemical Research Center | Process for producing peptide |
| DE2801238C2 (de) * | 1977-01-27 | 1986-06-05 | (Zaidanhojin) Sagami Chemical Research Center, Tokio/Tokyo | Verfahren zur Herstellung von Salzen aus L,L-Dipeptiden und Phenylalaninestern |
| JPS6022919B2 (ja) * | 1978-07-27 | 1985-06-04 | 財団法人相模中央研究所 | Ｎ―ベンジルオキシカルボニル‐ｌ‐アスパチル‐ｌ‐フエニルアラニンメチルエステルとフエニルアラニンメチルエステルとの付加化合物の製造方法 |
| JPS6022918B2 (ja) * | 1978-07-27 | 1985-06-04 | 財団法人相模中央研究所 | Ｎ−ベンジルオキシカルボニル−ｌ−アスパルチル−ｌ−フェニルアラニンメチル−エステルとフェニルアラニンメチルエステルとの付加化合物の製造方法 |
| JPS55135595A (en) * | 1979-04-03 | 1980-10-22 | Toyo Soda Mfg Co Ltd | Preparation of dipeptide |
| US4506011A (en) * | 1981-09-05 | 1985-03-19 | Toyo Soda Manufacturing Co., Ltd. | Process for preparation of aspartylphenylalanine alkyl esters |
-
1982
- 1982-02-01 JP JP57014699A patent/JPS57146595A/ja active Pending
- 1982-02-01 DE DE19823203292 patent/DE3203292A1/de active Granted
- 1982-02-01 GB GB8202814A patent/GB2092161B/en not_active Expired
- 1982-02-01 IE IE220/82A patent/IE52242B1/en unknown
- 1982-02-02 FR FR8201664A patent/FR2499098A1/fr active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB2092161A (en) | 1982-08-11 |
| DE3203292A1 (de) | 1982-09-16 |
| FR2499098A1 (fr) | 1982-08-06 |
| DE3203292C2 (enrdf_load_stackoverflow) | 1990-01-11 |
| JPS57146595A (en) | 1982-09-10 |
| IE820220L (en) | 1982-08-02 |
| GB2092161B (en) | 1984-08-01 |
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