GB1497248A - Process for removing n-formyl masking groups from esters - Google Patents
Process for removing n-formyl masking groups from estersInfo
- Publication number
- GB1497248A GB1497248A GB32945/76A GB3294576A GB1497248A GB 1497248 A GB1497248 A GB 1497248A GB 32945/76 A GB32945/76 A GB 32945/76A GB 3294576 A GB3294576 A GB 3294576A GB 1497248 A GB1497248 A GB 1497248A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- ester
- formyl
- organic solvent
- butanol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000002148 esters Chemical class 0.000 title abstract 7
- 238000000034 method Methods 0.000 title abstract 3
- 230000000873 masking effect Effects 0.000 title 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 5
- 239000003960 organic solvent Substances 0.000 abstract 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 abstract 2
- 238000010494 dissociation reaction Methods 0.000 abstract 2
- 230000005593 dissociations Effects 0.000 abstract 2
- 108090000765 processed proteins & peptides Proteins 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 125000003158 alcohol group Chemical group 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- -1 aliphatic ketones Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000007519 polyprotic acids Polymers 0.000 abstract 1
- 150000003138 primary alcohols Chemical class 0.000 abstract 1
- 150000003333 secondary alcohols Chemical class 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 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
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/12—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by hydrolysis, i.e. solvolysis in general
- C07K1/122—Hydrolysis with acids different from HF
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)
- Analytical Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50098817A JPS5223001A (en) | 1975-08-14 | 1975-08-14 | Process for elimination of formyl group |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1497248A true GB1497248A (en) | 1978-01-05 |
Family
ID=14229861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB32945/76A Expired GB1497248A (en) | 1975-08-14 | 1976-08-06 | Process for removing n-formyl masking groups from esters |
Country Status (9)
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX4704E (es) * | 1976-12-27 | 1982-08-04 | Monsanto Co | Procedimiento mejorado para la preparacion de ester metilico de alfa-l-aspartil-l-fenilalanina |
| JPS57125891U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1981-01-31 | 1982-08-05 | ||
| JPS57131746A (en) * | 1981-02-10 | 1982-08-14 | Ajinomoto Co Inc | Removal of n-formyl group |
| IE810577L (en) * | 1983-05-31 | 1982-09-16 | Prendergast Angela | Apparatus for fermentation |
| IT1194795B (it) * | 1981-05-13 | 1988-09-28 | Pierrel Spa | Procedimento per la eliminazione del gruppo n-formile da peptidi n-formilati e da esteri di peptidi n-formilati |
| JPS5821687U (ja) * | 1981-08-03 | 1983-02-10 | 新日軽株式会社 | 建具 |
| JPH03169894A (ja) * | 1982-04-22 | 1991-07-23 | Ajinomoto Co Inc | α―Ｌ―アスパルチル―Ｌ―フェニルアラニンメチルエステルまたはその塩酸塩の製法 |
| JPS58185545A (ja) * | 1982-04-22 | 1983-10-29 | Ajinomoto Co Inc | α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステルまたはその塩酸塩の製法 |
| GB8321802D0 (en) * | 1983-08-12 | 1983-09-14 | Erba Farmitalia | Aspartame synthesis |
| JPH07636B2 (ja) * | 1984-12-17 | 1995-01-11 | 三井東圧化学株式会社 | Ｎ−ホルミル−α−アスパルチルフエニルアラニンの製造法 |
| ES8703487A1 (es) * | 1984-12-27 | 1987-03-01 | Mitsui Toatsu Chemicals | Procedimiento para la preparacion de a-l-aspartil-l-fenila- lanina metil ester |
| AU561384B2 (en) * | 1985-03-26 | 1987-05-07 | Mitsui Toatsu Chemicals Inc. | Preparation of -l-aspartyl-l-phenylalanine methyl ester or hydrochloride thereof |
| IT1190395B (it) * | 1985-09-30 | 1988-02-16 | Lark Spa | Procedimento per la rimozione del gruppo formile da un estere di n-formil peptide o di n-formil amminoacido |
| JPH0680075B2 (ja) * | 1985-12-24 | 1994-10-12 | 味の素株式会社 | Ｎ―ホルミル―α―Ｌ―アスパルチル―Ｌ―フェニルアラニンメチルエステルの製造法 |
| DE3780585T2 (de) * | 1986-12-05 | 1993-03-18 | Mitsui Toatsu Chemicals | Herstellung von alpha-l-aspartyl-l-phenylalanin-methylester oder deren hydrohalide. |
| JPH0832719B2 (ja) * | 1986-12-19 | 1996-03-29 | 三井東圧化学株式会社 | 吸湿性の小さいα−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステルの製造法 |
| IT1270852B (it) * | 1992-08-27 | 1997-05-13 | Miwon Co Ltd | Procedimento per la produzione dell'estere metilico di alfa-l-aspartil-l-fenilalanina. |
| AU2002314773B2 (en) * | 2001-05-09 | 2008-05-01 | Celmed Oncology (Usa), Inc. | Peptide deformylase activated prodrugs |
| CN1662238A (zh) * | 2002-04-18 | 2005-08-31 | 塞米得肿瘤学美国公司 | 肽去甲酰酶活化的前体药物 |
| BR0315537A (pt) * | 2002-11-14 | 2005-09-27 | Celmed Oncology Usa Inc | Pró-drogas ativadas por peptìdeo desformilase |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2053188C3 (de) * | 1970-10-29 | 1979-11-22 | Ajinomoto Co. Inc., Tokio | Verfahren zur Herstellung von Niederalkylestern des a -L-Asparagyl- L-phenylalanins |
| US3933781A (en) * | 1973-11-05 | 1976-01-20 | Monsanto Company | Process for the preparation of α-L-aspartyl-L-phenylalanine alkyl esters |
| JPS5823380B2 (ja) * | 1974-12-05 | 1983-05-14 | 味の素株式会社 | ホルミルキノ ダツリホウ |
-
1975
- 1975-08-14 JP JP50098817A patent/JPS5223001A/ja active Granted
-
1976
- 1976-08-06 GB GB32945/76A patent/GB1497248A/en not_active Expired
- 1976-08-06 AU AU16636/76A patent/AU499510B2/en not_active Expired
- 1976-08-10 DE DE2635948A patent/DE2635948C2/de not_active Expired
- 1976-08-10 US US05/713,270 patent/US4071511A/en not_active Expired - Lifetime
- 1976-08-12 FR FR7624681A patent/FR2320934A1/fr active Granted
- 1976-08-12 NL NL7608965A patent/NL7608965A/xx not_active Application Discontinuation
- 1976-08-13 CH CH1035976A patent/CH613687A5/xx not_active IP Right Cessation
- 1976-08-13 CA CA259,023A patent/CA1075680A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7608965A (nl) | 1977-02-16 |
| CA1075680A (en) | 1980-04-15 |
| AU499510B2 (en) | 1979-04-26 |
| CH613687A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-10-15 |
| DE2635948C2 (de) | 1985-11-14 |
| JPS5223001A (en) | 1977-02-21 |
| AU1663676A (en) | 1978-02-09 |
| FR2320934B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-05-23 |
| JPS5726588B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-06-05 |
| US4071511A (en) | 1978-01-31 |
| FR2320934A1 (fr) | 1977-03-11 |
| DE2635948A1 (de) | 1977-03-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19960805 |