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Boc-D-Orn(N3)-OH CHA - CAS 1858224-18-6

Boc-D-Orn(N3)-OH CHA - CAS 1858224-18-6 Catalog number: BADC-01785

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Boc-D-Orn(N3)-OH CHA is a derivative of D-ornithine with an azide (N3) group on the δ-amino group and a Boc (tert-butyloxycarbonyl) protecting group on the α-amino group. It exists as a cyclohexylamine (CHA) salt. This compound is used in peptide synthesis and bioconjugation for introducing azide-functionalized residues that can participate in click chemistry reactions, enabling site-specific modifications and functionalization.

Category
ADC Linker
Product Name
Boc-D-Orn(N3)-OH CHA
CAS
1858224-18-6
Catalog Number
BADC-01785
Molecular Formula
C16H31N5O4
Molecular Weight
357.45
Purity
>98%
Boc-D-Orn(N3)-OH CHA

Ordering Information

Catalog Number Size Price Quantity
BADC-01785 -- $-- Inquiry
Synonyms
Boc-D-Orn(N3).CHA; (R)-Boc-2-amino-5-azido-pentanoic acid CHA salt; Boc-D-azidonorvaline CHA salt; Boc-D-Nva(5-N3).CHA; D-Norvaline, 5-azido-N-[(1,1-dimethylethoxy)carbonyl]-, compd. with cyclohexanamine (1:1); Boc-D-Orn(N3) CHA salt; N-alpha-t-Butyloxycarbonyl-delta-azido-D-ornithine cyclohexylamine; (R)-2-t-Butyloxycarbonylamino-5-azidopentanoic acid cyclohexylamine; (R)-5-Azido-2-((tert-butoxycarbonyl)amino)pentanoic acid cyclohexylamine
IUPAC Name
(2R)-5-azido-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid;cyclohexanamine
Canonical SMILES
CC(C)(C)OC(=O)N[C@H](CCCN=[N+]=[N-])C(=O)O.C1CCC(CC1)N
InChI
InChI=1S/C10H18N4O4.C6H13N/c1-10(2,3)18-9(17)13-7(8(15)16)5-4-6-12-14-11;7-6-4-2-1-3-5-6/h7H,4-6H2,1-3H3,(H,13,17)(H,15,16);6H,1-5,7H2/t7-;/m1./s1
InChIKey
OTASSZHMIDGDAW-OGFXRTJISA-N
Storage
Store at 2-8 °C
Related CAS
1858224-17-5 (free base)

Boc-D-Orn(N3)-OH (CHA), a versatile compound widely employed in chemical biology and medicinal chemistry, boasts diverse applications across multiple domains. Here are four key applications of Boc-D-Orn(N3)-OH (CHA), presented with high perplexity and burstiness:

Chemical Synthesis: Acting as a cornerstone in peptide synthesis, Boc-D-Orn(N3)-OH (CHA) serves as a protected derivative of amino acids. The Boc protective group imparts stability during synthesis, while the azide group facilitates subsequent bio-orthogonal reactions. This compound stands as a pivotal building block for crafting intricate peptide structures and functionalized biomolecules, showcasing its profound significance in the realm of chemical synthesis applications.

Click Chemistry: Within the domain of click chemistry, the azide group within Boc-D-Orn(N3)-OH (CHA) plays a pivotal and indispensable role in reactions like the azide-alkyne cycloaddition. These reactions exhibit unparalleled efficiency and compatibility with a wide array of biological conditions, enabling the formation of biomolecular conjugates. This application is essential for various purposes such as labeling, imaging, and the development of cutting-edge bioconjugates for both research and therapeutic pursuits.

Drug Development: In the dynamic arena of drug development, Boc-D-Orn(N3)-OH (CHA) contributes significantly to the creation of prodrugs and innovative drug delivery systems. Tailoring the azide group allows for the attachment of therapeutic agents or targeting moieties, enhancing drug efficacy and selectivity. This strategic approach empowers controlled release and targeted therapy, offering substantial benefits in treating diverse diseases through the utilization of Boc-D-Orn(N3)-OH (CHA).

Proteomics: Within the intricate landscape of proteomics research, Boc-D-Orn(N3)-OH (CHA) finds invaluable utility in site-specific protein labeling. The azide moiety interacts seamlessly with alkynes to affix fluorescent probes or other tags, facilitating the exploration of protein interactions and functions. This application plays a pivotal role in unraveling protein dynamics and illuminating protein networks, underscoring the critical importance of Boc-D-Orn(N3)-OH (CHA) in advancing the field of proteomics studies.

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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