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Boc-D-Dap(N3) CHA salt

  CAS No.: 2098496-96-7   Cat No.: BADC-01762   Purity: ≥99% by HPLC 4.5  

Boc-D-Dap(N3) CHA salt is a Boc-protected D-diaminopropionic acid derivative with an azide group on the side chain, existing as a cyclohexylamine salt. The azide group enables 'click chemistry' reactions for site-specific peptide/protein modification, while the Boc group protects the α-amino group during synthesis. This compound is used as a building block for synthesizing peptides that can be selectively modified via Staudinger ligation or click chemistry, and it has applications in bioconjugation, drug delivery systems, and peptide-based biomaterials.

Boc-D-Dap(N3) CHA salt

Structure of 2098496-96-7

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Molecular Formula
C14H27N5O4
Molecular Weight
329.40
Shipping
Store at 2-8 °C

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Synonyms
N-alpha-Boc-N-beta-azido-D-2,3-diaminopropionic acid cyclohexylamine salt; Boc-D-beta-azidoalanine CHA salt; Boc-D-Dap(N3).CHA; Boc-D-Dpr(N3).CHA; Boc-D-Dapa(N3).CHA; Nα-Boc-Nβ-Azido-D-2,3-diaminopropionic acid cyclohexylammonium salt; Boc-D-Ala(N3) CHA; Boc-D-Aza-OH (CHA); N-alpha-t-Butyloxycarbonyl-3-azido-D-alanine cyclohexylamine salt; D-Alanine, 3-azido-N-[(1,1-dimethylethoxy)carbonyl]-, compd. with cyclohexanamine (1:1); (R)-2-t-Butyloxycarbonylamino-3-azidopropanoic acid cyclohexylamine; Boc-D-beta-azidoalanine cyclohexylamine
IUPAC Name
(2R)-3-azido-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;cyclohexanamine
Canonical SMILES
CC(C)(C)OC(=O)N[C@H](CN=[N+]=[N-])C(=O)O.C1CCC(CC1)N
InChI
InChI=1S/C8H14N4O4.C6H13N/c1-8(2,3)16-7(15)11-5(6(13)14)4-10-12-9;7-6-4-2-1-3-5-6/h5H,4H2,1-3H3,(H,11,15)(H,13,14);6H,1-5,7H2/t5-;/m1./s1
InChIKey
YDTIDHZIISJNBU-NUBCRITNSA-N
Melting Point
122-128 °C
Appearance
White crystalline powder
Storage
Store at 2-8 °C

Boc-D-Aza-OH (CHA) is widely used in peptide synthesis as a protecting group for the amino function. This N-Boc-protected azetidine derivative ensures that the amino group remains unreactive during various synthetic steps while allowing for selective deprotection at a later stage. The use of Boc-D-Aza-OH (CHA) in peptide synthesis enhances the overall efficiency and specificity of the process, making it an essential compound for the development of complex peptides and proteins. Its stability under both acidic and basic conditions adds to its versatility in synthetic applications.

In medicinal chemistry, Boc-D-Aza-OH (CHA) is employed in the design and synthesis of enzyme inhibitors and receptor antagonists. By incorporating this compound into the molecular framework, researchers can explore new avenues in drug discovery and development. The unique structural attributes of Boc-D-Aza-OH (CHA) contribute to its ability to interact with biological targets in a highly selective manner, thus paving the way for the creation of novel therapeutic agents. This application is particularly important in the development of drugs targeting proteases, kinases, and other critical enzymes involved in disease pathogenesis.

Boc-D-Aza-OH (CHA) finds significant use in the field of chemical biology, especially in the study of protein-protein interactions. By utilizing this compound as a building block, scientists can generate peptide mimetics that modulate or inhibit specific protein interactions. This capability is crucial for understanding cellular processes and for the development of tools that can probe or alter biological systems with high precision. The versatility of Boc-D-Aza-OH (CHA) thus makes it a valuable resource in the toolbox of chemical biologists working on intricate biological questions.

Additionally, Boc-D-Aza-OH (CHA) is instrumental in the development of bioactive natural product analogs. Researchers use this compound to modify and improve the properties of natural products, which often serve as lead compounds in drug discovery. By integrating Boc-D-Aza-OH (CHA) into the structure of natural products, it is possible to enhance their stability, bioavailability, and target specificity. This application not only broadens the scope of natural product research but also contributes to the identification of promising candidates for therapeutic development.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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