IT1142823B - Enzymatic esterification of alpha-L-aspartyl-L-phenylalanine - Google Patents
Enzymatic esterification of alpha-L-aspartyl-L-phenylalanineInfo
- Publication number
- IT1142823B IT1142823B IT49313/81A IT4931381A IT1142823B IT 1142823 B IT1142823 B IT 1142823B IT 49313/81 A IT49313/81 A IT 49313/81A IT 4931381 A IT4931381 A IT 4931381A IT 1142823 B IT1142823 B IT 1142823B
- Authority
- IT
- Italy
- Prior art keywords
- aspartyl
- enzyme
- phenylalanine
- alpha
- esterification
- Prior art date
Links
- 230000032050 esterification Effects 0.000 title abstract 3
- 238000005886 esterification reaction Methods 0.000 title abstract 3
- YZQCXOFQZKCETR-UWVGGRQHSA-N Asp-Phe Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 YZQCXOFQZKCETR-UWVGGRQHSA-N 0.000 title abstract 2
- 230000002255 enzymatic effect Effects 0.000 title 1
- 108090000790 Enzymes Proteins 0.000 abstract 3
- 102000004190 Enzymes Human genes 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 108090000371 Esterases Proteins 0.000 abstract 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 abstract 1
- 108091005804 Peptidases Proteins 0.000 abstract 1
- 102000035195 Peptidases Human genes 0.000 abstract 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 abstract 1
- 108010056079 Subtilisins Proteins 0.000 abstract 1
- 102000005158 Subtilisins Human genes 0.000 abstract 1
- 108010051873 alkaline protease Proteins 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- -1 aspartyl ester Chemical class 0.000 abstract 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 235000003599 food sweetener Nutrition 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 229960005190 phenylalanine Drugs 0.000 abstract 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 abstract 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 1
- 239000003765 sweetening agent Substances 0.000 abstract 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Esterification of alpha-L-aspartyl -L-phenylalanine (I) is effected by contact with an alcohol (II) in presence of a proteolytic enzyme with specific esterase activity in aq. (II) medium at pH 4-7. The (II) concn. is sufficiently high to reverse the hydrolytic activity of the enzyme. The enzyme is pref. a serine alkaline proteinase, esp. subtilisin Carlsberg. Typically the alcohol is MeOH at 10-90% concn. The (I) may be replaced by N-protected- alpha-L-aspartyl-L-phenylaline, and after esterification the protecting gp. is removed, e.g. a benzyloxycarbonyl gp. is used for protection. The enzyme may be used in free form or in immobilised form in the usual way. Reaction is at 10-50 deg.C. The COOH gp. of the phenylalanine is selectively alkylated in a single phase system, without formation of diester or aspartyl ester. The alkyl ester of (I) are known sweetening agents.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT49313/81A IT1142823B (en) | 1981-09-17 | 1981-09-17 | Enzymatic esterification of alpha-L-aspartyl-L-phenylalanine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT49313/81A IT1142823B (en) | 1981-09-17 | 1981-09-17 | Enzymatic esterification of alpha-L-aspartyl-L-phenylalanine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IT8149313A0 IT8149313A0 (en) | 1981-09-17 |
| IT1142823B true IT1142823B (en) | 1986-10-15 |
Family
ID=11270307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT49313/81A IT1142823B (en) | 1981-09-17 | 1981-09-17 | Enzymatic esterification of alpha-L-aspartyl-L-phenylalanine |
Country Status (1)
| Country | Link |
|---|---|
| IT (1) | IT1142823B (en) |
-
1981
- 1981-09-17 IT IT49313/81A patent/IT1142823B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| IT8149313A0 (en) | 1981-09-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TA | Fee payment date (situation as of event date), data collected since 19931001 |
Effective date: 19970929 |