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γ−Amino acids

(3S,4S)-4-Amino-3-hydroxy-5-phenylpentanoic acid

CAS 72155-50-1
Catalog BAT-007767
Molecular Weight 209.24
Molecular Formula C11H15NO3
(3S,4S)-4-Amino-3-hydroxy-5-phenylpentanoic acid

4-Amino-3-hydroxybutyric acid

CAS 924-49-2
Catalog BAT-007850
Molecular Weight 119.12
Molecular Formula C4H9NO3
4-Amino-3-hydroxybutyric acid

Acetyl-γ-aminobutyric acid

CAS 3025-96-5
Catalog BAT-007901
Molecular Weight 145.16
Molecular Formula C6H11NO3
Acetyl-γ-aminobutyric acid

Boc-(3S,4S)-4-amino-3-hydroxy-5-(3-indolyl)pentanoic acid

CAS 109579-23-9
Catalog BAT-007918
Molecular Weight 348.39
Molecular Formula C18H24N2O5
Boc-(3S,4S)-4-amino-3-hydroxy-5-(3-indolyl)pentanoic acid

Boc-(3S,4S)-4-amino-3-hydroxy-5-(4-benzyloxyphenyl)pentanoic acid

CAS 204195-38-0
Catalog BAT-007919
Molecular Weight 415.48
Molecular Formula C23H29NO4
Boc-(3S,4S)-4-amino-3-hydroxy-5-(4-benzyloxyphenyl)pentanoic acid

Boc-(3S,4S)-4-amino-3-hydroxy-5-cyclohexylpentanoic acid

CAS 98105-45-4
Catalog BAT-007920
Molecular Weight 315.41
Molecular Formula C16H29NO5
Boc-(3S,4S)-4-amino-3-hydroxy-5-cyclohexylpentanoic acid

Boc-(3S,4S)-4-amino-3-hydroxy-5-methylhexanoic acid dicyclohexylammonium salt

CAS 204192-31-4
Catalog BAT-007921
Molecular Weight 442.63
Molecular Formula C12H23NO5·C12H23N
Boc-(3S,4S)-4-amino-3-hydroxy-5-methylhexanoic acid dicyclohexylammonium salt

Boc-(3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid

CAS 72155-48-7
Catalog BAT-007922
Molecular Weight 309.36
Molecular Formula C16H23NO5
Boc-(3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid

Boc-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid

CAS 58521-49-6
Catalog BAT-007923
Molecular Weight 275.34
Molecular Formula C13H25NO5
Boc-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid

Boc-(R)-4-amino-5-phenylpentanoic acid

CAS 195867-20-0
Catalog BAT-007925
Molecular Weight 293.36
Molecular Formula C16H23NO4
Boc-(R)-4-amino-5-phenylpentanoic acid

Boc-(R)-4-amino-6-methyl-heptanoic acid

CAS 146453-32-9
Catalog BAT-007926
Molecular Weight 259.34
Molecular Formula C13H25NO4
Boc-(R)-4-amino-6-methyl-heptanoic acid

Vigabatrin EP Impurity D

CAS 56-12-2
Catalog BAT-008079
Molecular Weight 103.12
Molecular Formula C4H9NO2
Vigabatrin EP Impurity D

Boc-S-(γ)-Phe

CAS 790223-54-0
Catalog BAT-008358
Molecular Weight 293.36
Molecular Formula C16H23NO4
Boc-S-(γ)-Phe

R-(γ)-Phe

CAS 63328-06-3
Catalog BAT-008639
Molecular Weight 193.24
Molecular Formula C11H15NO2
R-(γ)-Phe

S-(γ)-Phe

CAS 916198-97-5
Catalog BAT-008641
Molecular Weight 193.24
Molecular Formula C11H15NO2
S-(γ)-Phe

(S)-Boc-4-amino-pentanoic acid

CAS 207924-92-3
Catalog BAT-008793
Molecular Weight 217.26
Molecular Formula C10H19NO4
(S)-Boc-4-amino-pentanoic acid

Me-DL-Glu-OH

CAS 35989-16-3
Catalog BAT-008906
Molecular Weight 161.16
Molecular Formula C6H11NO4
Me-DL-Glu-OH

(R)-Fmoc-4-amino-5-(3-indolyl)pentanoic acid

CAS 917099-01-5
Catalog BAT-008921
Molecular Weight 454.5
Molecular Formula C28H26N2O4
(R)-Fmoc-4-amino-5-(3-indolyl)pentanoic acid

(S)-Boc-3-amino-4,4,4-trifluoro-butyric acid

CAS 1310680-43-3
Catalog BAT-009014
Molecular Weight 257.21
Molecular Formula C9H14F3NO4
(S)-Boc-3-amino-4,4,4-trifluoro-butyric acid

4-Boc-amino-2,2-dimethylbutyric acid

CAS 153039-17-9
Catalog BAT-009045
Molecular Weight 231.29
Molecular Formula C11H21NO4
4-Boc-amino-2,2-dimethylbutyric acid

Introduction

γ-amino acids are classes of amino acids classified by the positions of amino and carboxyl. γ-amino acids have both linear forms, and amino and carboxyl groups are separated or combined into a cyclic structure. Because γ-amino acid are a class of biologically active compounds in the central nervous system of mammals, it has attracted extensive attention from researchers. γ-amino butyric acid (GABA) analogs are a very important kind of γ-amino acids, thus the researchers' study on γ-amino acids mainly focuse on the synthesis of γ-amino butyric acid analogs by asymmetric methods starting from unsaturated compounds for using in clinical research. The inhibitor neurotransmitter g-amino butyric acid is a structural template for many substances that have an effect on the central nervous system. A common strategy for designing these compounds is to manipulate the γ-amino butyric acid molecule to increase its lipophilicity, thus allowing it to enter the central nervous system.

Applications

Medicine: Protease inhibitors: The structure type of β-hydroxy-γ-amino acids have been the focus of research in recent years, especially in the development of new drugs based on protease inhibitors. (1) Sedative nerves and anti-anxiety: The most widely studied γ-amino acid is γ-aminobutyric acid, which can reduce neuronal activity and prevent nerve cells from overheating. It can bind to and activate anxiolytic brain receptors, and then cooperate with other substances to prevent anxiety-related information from reaching the central nervous system of brain. (2) Lower blood pressure: γ-amino acids can act on the vascular motor center of the spinal cord, effectively promote vasodilation and achieve the purpose of lowering blood pressure. (3) Lower blood ammonia: γ-amino acids can also inhibit the decarboxylation reaction of glutamic acid and lower blood ammonia. More glutamic acid combines with ammonia to produce urea and excreted from the body to relieve ammonia poisoning, thereby improving liver function. (4) Treatment of mental illness: When the concentration of γ-amino butyric acid in the human body is too low, it will cause epilepsy, Huntington's disease and Parkinson's disease. Ingestion of γ-amino butyric acid can increase the activity of glucose phosphatase, make brain cells active, promote metabolism of brain tissue and restore brain cell function, and improve nerve function. Therefore, such γ-amino acids have a pharmacological effect in clinical treatment of related diseases.

Animal husbandry: γ-aminobutyric acid has the effects of improving animal harvest, improving carcass quality, enhancing immune function, reproductive performance and anti-hypoxia ability, and relieving heat stress.

Food industry: Adding γ-aminobutyric acid as an additive to dairy products can further enhance the functionality of dairy products.

References:

  1. Gante, J. Angew. Chem. Int. Ed. Engl. 1994, 33, 1699.
  2. Adang, A. E. P.; Hermkens, P. H. H.; Linders, J. T. M.; Ottenheim, H. C. J.; van Staveren, C. J. Recl. Trav. Chim. Pays-Bas 1994, 113, 63.

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