159991-23-8

Basic information

• Product Name: (R)-N-BOC-3-AMINOBUTYRIC ACID
• Synonyms: BOC-D-BETA-HOMOALANINE;BOC-D-B-HOMOALA-OH;BOC PROTECTED (R)-B-AMINOBUTYRIC ACID;3-N-BOC-3-(R)-AMINO BUTYRIC ACID;(R)-N-BOC-3-AMINOBUTYRIC ACID;(R)-N-(TERT-BUTOXYCARBONYL)-3-AMINOBUTYRIC ACID;(R)-BOC-B2-HOALA-OH;(R)-BOC-BETA2-HAL-OH
• CAS NO: 159991-23-8
• Molecular Formula: C₉H₁₇NO₄
• Molecular Weight: 203.24
• Product Categories: N-BOC;Beta amino acids;pharmacetical;Amino Acid
• Mol File: 159991-23-8.mol
• Article Data: 31

Chemical Properties

• Melting Point: 104-107 °C
• Boiling Point: 339.5 °C at 760 mmHg
• Flash Point: 159.1 °C
• Appearance: /
• Density: 1.101 g/cm³
• Vapor Pressure: 1.69E-05mmHg at 25°C
• Refractive Index: 1.46
• Storage Temp.: Store at 0-5°C
• PKA: 4.43±0.10(Predicted)
• CAS DataBase Reference: (R)-N-BOC-3-AMINOBUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N-BOC-3-AMINOBUTYRIC ACID(159991-23-8)
• EPA Substance Registry System: (R)-N-BOC-3-AMINOBUTYRIC ACID(159991-23-8)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• Hazardous Substances Data: 159991-23-8(Hazardous Substances Data)

Usage

Description

(R)-N-BOC-3-AMINOBUTYRIC ACID, also known as (R)-3-(tert-Butoxycarbonylamino)butanoic Acid, is a non-proteinogenic amino acid derived from the naturally occurring amino acid, beta-alanine. It is characterized by its off-white powder form and is primarily used in the synthesis of peptide analogs. (R)-N-BOC-3-AMINOBUTYRIC ACID is valuable in the field of pharmaceuticals and biochemistry due to its unique structural properties and potential applications in drug development.

Uses

Used in Pharmaceutical Industry:
(R)-N-BOC-3-AMINOBUTYRIC ACID is used as a building block for the synthesis of peptide analogs, which are essential in the development of new drugs and therapeutic agents. Its application in this industry is crucial for creating novel compounds with potential medicinal properties.
Used in Biochemical Research:
In the field of biochemistry, (R)-N-BOC-3-AMINOBUTYRIC ACID serves as a valuable research tool for studying the structure and function of proteins and peptides. Its unique properties allow scientists to investigate various aspects of protein folding, stability, and interactions with other biomolecules.
Used in Drug Delivery Systems:
Similar to gallotannin, (R)-N-BOC-3-AMINOBUTYRIC ACID can be employed in the development of innovative drug delivery systems. These systems aim to improve the bioavailability, targeting, and overall efficacy of peptide-based therapeutics by utilizing (R)-N-BOC-3-AMINOBUTYRIC ACID as a key component in the design and synthesis of drug carriers.

InChI:InChI=1/C9H17NO4/c1-6(5-7(11)12)10-8(13)14-9(2,3)4/h6H,5H2,1-4H3,(H,10,13)(H,11,12)/t6-/m1/s1

Upstream product

• 186521-98-2 N-[(1R)-3-diazo-1-methyl-2-oxopropyl]carbamic acid tert-butyl ester 
• 159877-47-1 methyl 3-(R)-[N-(tert-butoxycarbonyl)amino]-propanoate 
• 869468-34-8 (+)-(4R)-4-[(tert-butoxycarbonyl)amino]pentan-2-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 28267-25-6 (RS)-2-(aminomethyl)propanoic acid hydrochloride 
• 58610-42-7 (R)-3-aminobutanoic acid hydrochloride 
• 3775-73-3 (R)-3-aminobutanoic acid 
• 3744-87-4 Boc-(R)-Ala 
• 186581-53-3 diazomethane 
• 170367-68-7 (2-cyano-1(R)-methylethyl)carbamic acid, 1,1-dimethylethyl ester 
• 43080-09-7 3-t-butoxycarbonylaminobutyric acid 
• 34619-03-9 tert-butyldicarbonate 

Downstream Products

• 159877-48-2 (R)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]butanamide 
• 934525-68-5 C₁₈H₂₈N₂O₃ 
• 918964-88-2 3-(3-tert-butoxycarbonylamino-butyrylamino)-4-phenyl-butyric acid benzyl ester 
• 918964-82-6 3-(3-tert-butoxycarbonylamino-butyrylamino)-4-phenyl-butyric acid 4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl)-benzyl ester 
• 193071-09-9 (S)-2-((R)-3-tert-Butoxycarbonylamino-butyryloxy)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-2-(3-chloro-4-methoxy-phenyl)-1-(2,2,2-trichloro-ethoxycarbonyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester 
• 220760-44-1 (S)-2-((R)-3-tert-Butoxycarbonylamino-butyrylamino)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-2-(3-chloro-4-methoxy-phenyl)-1-(2,2,2-trichloro-ethoxycarbonyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester 
• 159877-49-3 (R)-3-[[(1,1-dimethylethoxy)carbonyl]amino]butanethioamide 
• 497861-77-5 (+)-tert-butyl [(R)-1-methyl-3-oxopropyl]carbamate 
• 167216-17-3 (-)-tert-butyl [(R)-3-hydroxy-1-methylpropyl]carbamate 
• 163188-28-1 benzyl N-Boc-(3R)-aminobutanoate 
• 193635-07-3 tert-butyl (S)-(4-oxopentan-2-yl)carbamate 

Relevant articles and documents

Synthesis and biological activity evaluation of azacycloheptane sulfonamide derivatives as potential orexin receptor antagonists

As the orexin signaling system is crucial for the regulation of the sleep/wake cycle, inhibitors of orexin-1 and orexin-2 receptors are of significant interest in the treatment of insomnia. Herein, a series of novel azacycloheptane sulfonamide derivatives were designed and synthesized, and all the compounds were evaluated as potential orexin receptor inhibitors by FLIPR Tetra calcium assay. A majority of the tested azacycloheptane sulfonamide derivatives showed OX1R and OX2R inhibitory activity. Chloro-substituted derivatives functionalized at the C5 or C6 position of the benzoxazole group exhibited better inhibitory activity for OX1R and OX2R than unsubstituted derivatives functionalized at C5 or C6. In addition, phenyl group modification had positive effects on the inhibitory activities, and an electron-withdrawing fluorine group at the ortho or meta position of the phenyl ring improved the OX2R inhibitory activity of the derivatives. This suggests that azacycloheptane sulfonamide derivatives are promising scaffolds for the development of OX1R and OX2R antagonists.

Isonitrile Formation by a Non-Heme Iron(II)-Dependent Oxidase/Decarboxylase

The electron-rich isonitrile is an important functionality in bioactive natural products, but its biosynthesis has been restricted to the IsnA family of isonitrile synthases. We herein provide the first structural and biochemical evidence of an alternative mechanism for isonitrile formation. ScoE, a putative non-heme iron(II)-dependent enzyme from Streptomyces coeruleorubidus, was shown to catalyze the conversion of (R)-3-((carboxymethyl)amino)butanoic acid to (R)-3-isocyanobutanoic acid through an oxidative decarboxylation mechanism. This work further provides a revised scheme for the biosynthesis of a unique class of isonitrile lipopeptides, of which several members are critical for the virulence of pathogenic mycobacteria.

Protein-protein interface mimicry by an oxazoline piperidine-2,4-dione

Representative minimalist mimics 1 were prepared from amino acids. Scaffold 1 was not designed to mimic any particular secondary structure, but simulated accessible conformations of this material were compared with common ideal secondary structures and with >125000 different protein-protein interaction (PPI) interfaces. This data mining exercise indicates that scaffolds 1 can mimic features of sheet-turn-sheets, somewhat fewer helical motifs, and numerous PPI interface regions that do not resemble any particular secondary structure.