Production Method 1

73259-81-1

94778-71-9

Reaction Conditions

1.1 Solvents: Ethanol ,  Water ;  10 min, 0 °C
1.2 Reagents: Sodium cyanoborohydride ;  overnight, rt

Reference

Peptide stapling with anion-π catalysts

Pham, Anh-Tuan; Matile, Stefan, Chemistry - An Asian Journal, 2020, 15(10), 1562-1566

Production Method 2

73259-81-1

94778-71-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ,  Water ;  21 - 23 °C; 48 h, 21 - 23 °C

Reference

Peptide-Catalyzed Conversion of Racemic Oxazol-5(4H)-ones into Enantiomerically Enriched α-Amino Acid Derivatives

Metrano, Anthony J.; Miller, Scott J., Journal of Organic Chemistry, 2014, 79(4), 1542-1554

Production Method 3

73259-81-1

94778-71-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol

Reference

Phe*-Ala-based pentapeptide mimetics are BACE inhibitors: P2 and P3 SAR

Lamar, Jason; Hu, Jingdan; Bueno, Ana Belen; Yang, Hsiu-Chiung; Guo, Deqi; et al, Bioorganic & Medicinal Chemistry Letters, 2004, 14(1), 239-243

Production Method 4

73259-81-1

94778-71-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ,  Water ;  24 h, rt

Reference

Cyclic peptide compounds with antagonistic PD-1/PD-L1 interaction and application thereof in preparing medicines for treating breast cancer and melanoma

, China, , ,

(2S)-2-{(tert-butoxy)carbonylamino}-3-(dimethylamino)propanoic acid Raw materials

• (2S)-3-amino-2-(tert-butoxycarbonylamino)propanoic acid

(2S)-2-{(tert-butoxy)carbonylamino}-3-(dimethylamino)propanoic acid Preparation Products

• (2S)-2-{(tert-butoxy)carbonylamino}-3-(dimethylamino)propanoic acid (94778-71-9)

• 1. Establishing the accuracy of position-specific carbon isotope analysis of propane by GC-pyrolysis-GC-IRMS
  ChangjieLiu,PengLiu,XiaofengWang,XiaoqiangLi,JuskeHorita
• 2. Emerging investigator series: bacteriophages as nano engineering tools for quality monitoring and pathogen detection in water and wastewater
  Fereshteh Bayat Environ. Sci.: Nano, 2021,8, 367-389
• 3. Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China?
  Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing Li Food Funct., 2018,9, 4234-4245
• 4. Evolutionary de novo design of phenothiazine derivatives for dye-sensitized solar cells?
  Vishwesh Venkatraman,Marco Foscato,Vidar R. Jensen,Bj?rn K?re Alsberg J. Mater. Chem. A, 2015,3, 9851-9860
• 5. Dissociation of aryl sulfonyl phthalimide radical anions: relevance to the biological activity of arylsulfonyl amides?
  Abdelaziz Houmam,Emad M. Hamed Chem. Commun., 2012,48, 11328-11330

• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Amino acids and derivatives

(2S)-2-{(tert-butoxy)carbonylamino}-3-(dimethylamino)propanoic acid (CAS No. 94778-71-9): An Overview

(2S)-2-{(tert-butoxy)carbonylamino}-3-(dimethylamino)propanoic acid (CAS No. 94778-71-9) is a versatile compound with significant applications in the fields of medicinal chemistry and pharmaceutical research. This compound, also known as Boc-protected L-methionine dimethylamide, is a valuable intermediate in the synthesis of peptides and other biologically active molecules. Its unique structure and properties make it an essential component in various research and development processes.

The chemical structure of (2S)-2-{(tert-butoxy)carbonylamino}-3-(dimethylamino)propanoic acid features a tert-butoxycarbonyl (Boc) protecting group on the amino group, which can be selectively removed under mild acidic conditions. This protecting group is widely used in peptide synthesis to prevent unwanted side reactions and ensure the desired sequence of amino acids. The dimethylamino group on the side chain imparts additional reactivity and functionality, making the compound suitable for a wide range of synthetic transformations.

Recent advancements in medicinal chemistry have highlighted the importance of (2S)-2-{(tert-butoxy)carbonylamino}-3-(dimethylamino)propanoic acid in the development of novel therapeutic agents. For instance, studies have shown that derivatives of this compound exhibit potent anti-inflammatory and anti-cancer properties. One notable example is the use of this compound as a building block in the synthesis of peptidomimetics, which are designed to mimic the biological activity of natural peptides while offering improved stability and pharmacokinetic properties.

In addition to its role in drug discovery, (2S)-2-{(tert-butoxy)carbonylamino}-3-(dimethylamino)propanoic acid has been extensively studied for its potential in protein engineering and biocatalysis. The ability to selectively modify amino acids with functional groups like the Boc protecting group and dimethylamino moiety allows researchers to create proteins with enhanced catalytic activity or altered substrate specificity. This has significant implications for the development of biocatalysts for industrial applications, such as the production of fine chemicals and pharmaceuticals.

The synthesis of (2S)-2-{(tert-butoxy)carbonylamino}-3-(dimethylamino)propanoic acid typically involves several steps, including the protection of the amino group with tert-butyldimethylsilyl (TBS) or tert-butoxycarbonyl (Boc) groups, followed by the introduction of the dimethylamino group through alkylation or reductive amination reactions. The final step involves deprotection to yield the desired product. These synthetic routes are well-documented in the literature and have been optimized for high yields and purity.

The physical and chemical properties of (2S)-2-{(tert-butoxy)carbonylamino}-3-(dimethylamino)propanoic acid are also well-characterized. It is a white crystalline solid that is soluble in common organic solvents such as dichloromethane, ethanol, and dimethylformamide (DMF). Its melting point, boiling point, and other thermodynamic properties have been determined through various analytical techniques, including nuclear magnetic resonance (NMR), mass spectrometry (MS), and X-ray crystallography.

In terms of safety and handling, (2S)-2-{(tert-butoxy)carbonylamino}-3-(dimethylamino)propanoic acid should be stored under dry conditions to prevent hydrolysis of the Boc protecting group. It is generally considered safe to handle under standard laboratory conditions, but appropriate personal protective equipment (PPE), such as gloves and safety goggles, should be used to minimize exposure.

The market demand for (2S)-2-{(tert-butoxy)carbonylamino}-3-(dimethylamino)propanoic acid has been steadily increasing due to its wide-ranging applications in pharmaceutical research and development. Major players in the industry are investing heavily in the synthesis and commercialization of this compound, driven by its potential to contribute to breakthroughs in drug discovery and biotechnology.

In conclusion, (2S)-2-{(tert-butoxy)carbonylamino}-3-(dimethylamino)propanoic acid (CAS No. 94778-71-9) is a critical compound with significant implications for various fields within chemistry and biology. Its unique structure and properties make it an indispensable tool for researchers working on peptide synthesis, drug discovery, protein engineering, and biocatalysis. As new applications continue to emerge, this compound is likely to play an increasingly important role in advancing scientific knowledge and developing innovative solutions for healthcare and industry.

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