Cas no 10270-94-7 ((S)-2-Amino-4-((tert-butoxycarbonyl)amino)butanoic Acid)

(S)-2-Amino-4-((tert-butoxycarbonyl)amino)butanoic Acid is a protected derivative of ornithine, featuring a Boc (tert-butoxycarbonyl) group on the δ-amino functionality. This compound is widely used in peptide synthesis, where the Boc group serves as a temporary protecting group for the amine, enabling selective deprotection under mild acidic conditions. Its chiral purity and stability make it valuable for constructing complex peptides and modified amino acid derivatives. The tert-butoxycarbonyl moiety enhances solubility in organic solvents, facilitating coupling reactions in solid-phase and solution-phase synthesis. This reagent is particularly useful in medicinal chemistry and biochemical research for introducing ornithine analogs into peptide backbones with high fidelity.
(S)-2-Amino-4-((tert-butoxycarbonyl)amino)butanoic Acid structure
10270-94-7 structure
Product Name:(S)-2-Amino-4-((tert-butoxycarbonyl)amino)butanoic Acid
CAS No:10270-94-7
MF:C9H18N2O4
MW:218.250222682953
MDL:MFCD00236842
CID:135293
PubChem ID:7019668
Update Time:2025-08-05

(S)-2-Amino-4-((tert-butoxycarbonyl)amino)butanoic Acid Chemical and Physical Properties

Names and Identifiers

    • Butanoic acid,2-amino-4-[[(1,1-dimethylethoxy)carbonyl]amino]-, (2S)-
    • (2S)-2-amino-4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
    • H-dab(boc)-oh
    • NGAMMA-BOC-L-2,4-DIAMINOBUTYRIC ACID
    • NG-BOC-L-2,4-DIAMINOBUTYRIC ACID
    • Nγ-Boc-L-2,4-diaminobutyric acid
    • (2S)-2-amino-4-[(tert-butoxycarbonyl)amino]butanoic acid
    • (2S)-Amino-4-[(tert-butoxycarbonyl)amino]butanoic acid
    • 4-<N-(tert-butoxycarbonyl)amino>-L-2,4-diaminobutyric acid
    • Butanoicacid,2-amino-4-[[(1,1-dimethylethoxy)carbonyl]amino]-,(S)
    • Butyric acid,2-amino-4-(carboxyamino)-,4-tert-butyl ester,L-(8CI)
    • H-Daba(Boc)-OH
    • Ng-(tert-butyloxycarbonyl)-L-2,4-diaminobutyric acid
    • Dab(Boc)-OH
    • L-Dab(Boc)-OH
    • H-L-Daba(Boc)-OH
    • N-GAMMA-BOC-L-2,4-DIAMINOBUTYRIC ACID
    • ALPHA,GAMMA-DIAMINOBUTYRIC ACID(BOC)-OH
    • (S)-2-amino-4-(tert-butoxycarbonylamino)butanoic acid
    • Butanoic acid, 2-amino-4-[[(1,1-dimethylethoxy)carbonyl]amino]-, (2S)-
    • (S)-2-Amino-4-(Boc-amino)butanoic Acid
    • AS-39243
    • MFCD00236842
    • AKOS022177993
    • (S)-2-amino-4-BOC-aminobutanoic acid
    • ICJFZQLAIOCZNG-LURJTMIESA-N
    • DTXSID80427150
    • SCHEMBL3916161
    • (2S)-2-azaniumyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
    • 10270-94-7
    • (S)-2-Amino-4-((tert-butoxycarbonyl)amino)butanoic acid
    • CS-0099795
    • Nγ-Boc-L-2,4-diaminobutyric acid≥ 99% (HPLC)
    • (S)-2-Amino-4-((tert-butoxycarbonyl)amino)butanoic Acid
    • MDL: MFCD00236842
    • Inchi: 1S/C9H18N2O4/c1-9(2,3)15-8(14)11-5-4-6(10)7(12)13/h6H,4-5,10H2,1-3H3,(H,11,14)(H,12,13)/t6-/m0/s1
    • InChI Key: ICJFZQLAIOCZNG-LURJTMIESA-N
    • SMILES: O(C(NCC[C@@H](C(=O)O)N)=O)C(C)(C)C

Computed Properties

  • Exact Mass: 218.12700
  • Monoisotopic Mass: 218.12665706g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 7
  • Complexity: 235
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -2.3
  • Topological Polar Surface Area: 102?2

Experimental Properties

  • Density: 1.160±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 216 oC
  • Solubility: Dissolution (44 g/l) (25 o C),
  • PSA: 101.65000
  • LogP: 1.40430

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Additional information on (S)-2-Amino-4-((tert-butoxycarbonyl)amino)butanoic Acid

Introduction to (S)-2-Amino-4-((tert-butoxycarbonyl)amino)butanoic Acid (CAS No. 10270-94-7)

(S)-2-Amino-4-((tert-butoxycarbonyl)amino)butanoic Acid, identified by its CAS number 10270-94-7, is a significant compound in the field of pharmaceutical chemistry and biochemistry. This compound, featuring a chiral center, has garnered considerable attention due to its utility as an intermediate in the synthesis of various pharmacologically active molecules. The presence of both amino and carbamate functional groups makes it a versatile building block for the development of novel therapeutic agents.

The (S)-configuration of this compound is particularly noteworthy, as enantiomeric purity is often crucial in drug development to ensure optimal biological activity and minimize adverse effects. The tert-butoxycarbonyl (Boc) group, a protecting group for amines, further enhances the compound's utility in multi-step synthetic routes. This protection allows for selective manipulation of other functional groups while maintaining the integrity of the amine moiety, which is essential in complex molecular constructions.

In recent years, there has been a growing interest in the development of peptidomimetics, which are synthetic analogs of natural peptides designed to mimic their biological functions but with improved pharmacokinetic properties. (S)-2-Amino-4-((tert-butoxycarbonyl)amino)butanoic Acid has been employed in the synthesis of such peptidomimetics due to its ability to incorporate into peptide chains with high fidelity. The rigid structure provided by the Boc group also aids in stabilizing the conformation of these mimetics, enhancing their binding affinity and selectivity.

Furthermore, this compound has found applications in the field of enzyme inhibition studies. Its structural motif closely resembles that of certain natural amino acids, making it an effective substrate or inhibitor for enzymes involved in metabolic pathways. For instance, researchers have utilized derivatives of (S)-2-Amino-4-((tert-butoxycarbonyl)amino)butanoic Acid to study the kinetics and mechanisms of amino acid transporters and metabolic enzymes. Such studies are pivotal in understanding disease pathologies and developing targeted therapies.

The synthesis of (S)-2-Amino-4-((tert-butoxycarbonyl)amino)butanoic Acid typically involves chiral resolution or asymmetric synthesis methods to ensure high enantiomeric purity. Advances in catalytic asymmetric transformations have enabled more efficient and scalable production processes for this compound. These methods often employ transition metal catalysts or biocatalysts, which offer superior selectivity and reduced environmental impact compared to traditional chemical synthesis routes.

In the context of drug discovery, (S)-2-Amino-4-((tert-butoxycarbonyl)amino)butanoic Acid has been incorporated into various lead compounds targeting different therapeutic areas. For example, its structural framework has been utilized in the design of protease inhibitors for antiviral and anticancer applications. The Boc group can be removed under specific conditions to introduce reactive amine functionalities, allowing further derivatization into more complex drug molecules.

Recent studies have also explored the use of (S)-2-Amino-4-((tert-butoxycarbonyl)amino)butanoic Acid in peptide-based therapeutics. Its ability to form stable peptide bonds and its compatibility with solid-phase peptide synthesis make it an attractive choice for constructing novel biologics. These therapeutics have shown promise in treating a range of diseases, including inflammatory disorders and neurodegenerative conditions.

The compound's role in medicinal chemistry extends beyond its use as a building block. It serves as a valuable tool for investigating protein-protein interactions and enzyme-substrate recognition. By modifying its structure or substituting functional groups, researchers can generate libraries of compounds with tailored properties for high-throughput screening assays. This approach has accelerated the discovery of new drug candidates by enabling rapid evaluation of large chemical spaces.

Additionally, (S)-2-Amino-4-((tert-butoxycarbonyl)amino)butanoic Acid has been employed in the development of new analytical methods for chiral separations. Techniques such as chromatography and spectroscopy benefit from its use as a reference standard or derivatization agent, improving the accuracy and reliability of enantiomeric purity assessments in pharmaceutical formulations.

As research continues to evolve, the applications of (S)-2-Amino-4-((tert-butoxycarbonyl)amino)butanoic Acid are expected to expand further. Emerging fields such as precision medicine and personalized therapeutics will likely leverage its unique structural features for designing bespoke treatments tailored to individual patient needs. The compound's versatility and well-documented synthetic protocols make it an indispensable asset in modern drug discovery pipelines.

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