GB927177A - Method for the temporary protection of amino groups - Google Patents
Method for the temporary protection of amino groupsInfo
- Publication number
- GB927177A GB927177A GB3052459A GB3052459A GB927177A GB 927177 A GB927177 A GB 927177A GB 3052459 A GB3052459 A GB 3052459A GB 3052459 A GB3052459 A GB 3052459A GB 927177 A GB927177 A GB 927177A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- group
- arginine
- carbobenzoxy
- protected
- 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
Classifications
-
- 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
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/061—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups
- C07K1/063—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups for alpha-amino functions
-
- 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
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/061—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups
- C07K1/064—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups for omega-amino or -guanidino functions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
Abstract
In the synthesis of peptides containing the arginyl radical <FORM:0927177/IV(a)/1> the guanidino-amino group is protected by reaction with an arylsulphonyl halide where-by one of the NG-hydrogen atoms is substituted by the arylsulphonyl radical; and the a -NH2 group is protected in the usual way by a radical which can be subsequently eliminated by hydrogenation. In examples, Na -carbobenzoxy-L-arginine is reacted with p-toluenesulphonyl chloride to yield Na -carbobenzoxy-NG-tosyl-L-arginine, the carbobenzoxy group of which is then eliminated by hydrogenation, in the presence of a palladium catalyst, to give <FORM:0927177/IV(a)/2> -tosyl-L-arginine. This compound is reacted with p-(p1-methoxyphenylazo)- benzyloxy-carbonyl chloride (=MZ-chloride) to yield <FORM:0927177/IV(a)/3> - arginine, which is then reacted with the methyl ester of L-tryptophyl-glycine and dicyclohexyl-carbodi-imide to give <FORM:0927177/IV(a)/4> - tosyl- L-arginyltryptophylglycine methyl ester. The MZ-group can be eliminated by catalytic hydrogenation, or by treatment with 3N-hydrogen bromide in glacial acetic acid. The specification mentions that the guanidino-amino group may be protected by a naphthalene sulphonyl radical; and that the a -NH2 group may be protected by the p-nitro-carbobenzoxy radical, or the p-(p1-nitronaphthylazo)- benzyloxycarbonyl radical.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6361459 | 1959-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB927177A true GB927177A (en) | 1963-05-29 |
Family
ID=4525111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3052459A Expired GB927177A (en) | 1959-09-05 | 1959-09-07 | Method for the temporary protection of amino groups |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB927177A (en) |
-
1959
- 1959-09-07 GB GB3052459A patent/GB927177A/en not_active Expired
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