N3-L-Cit-OH - CAS 1799421-66-1

N3-L-Cit-OH - CAS 1799421-66-1 Catalog number: BADC-01789

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N3-L-Cit-OH is a click chemistry reagent containing an azide group.

Category
ADCs Linker
Product Name
N3-L-Cit-OH
CAS
1799421-66-1
Catalog Number
BADC-01789
Molecular Formula
C6H11N5O3
Molecular Weight
201.18

Ordering Information

Catalog Number Size Price Quantity
BADC-01789 -- $-- Inquiry
Description
N3-L-Cit-OH is a click chemistry reagent containing an azide group.
IUPAC Name
(2S)-2-azido-5-(carbamoylamino)pentanoic acid
Canonical SMILES
C(CC(C(=O)O)N=[N+]=[N-])CNC(=O)N
InChI
InChI=1S/C6H11N5O3/c7-6(14)9-3-1-2-4(5(12)13)10-11-8/h4H,1-3H2,(H,12,13)(H3,7,9,14)/t4-/m0/s1
InChIKey
WTCIIDRGWZAPDA-BYPYZUCNSA-N

N3-L-Cit-OH is a key intermediate in peptide synthesis, particularly for incorporating citrulline, a non-proteinogenic amino acid, into peptides. Citrulline plays a vital role in various biological processes, such as nitric oxide synthesis, and the incorporation of N3-L-Cit-OH into peptides can impart unique biological functions. The N3-protection group ensures controlled deprotection during synthesis, making N3-L-Cit-OH a versatile building block for designing peptides with enhanced stability, selectivity, and bioactivity.

One of the primary applications of N3-L-Cit-OH is in the development of peptides that target specific biological pathways, especially in areas related to cardiovascular health and immune modulation. Citrulline, through its role in nitric oxide production, can influence vascular tone and blood flow. By incorporating N3-L-Cit-OH into therapeutic peptides, researchers can create peptide-based drugs that may help manage conditions such as hypertension, erectile dysfunction, and other vascular diseases. These peptides can provide a targeted, effective alternative to traditional drug therapies.

Another important application of N3-L-Cit-OH is in the synthesis of modified peptides for drug delivery systems. The incorporation of citrulline can enhance the solubility, stability, and pharmacokinetic properties of peptides. N3-L-Cit-OH can be used to create peptides that are more resistant to enzymatic degradation, making them more effective as drug candidates. Additionally, citrulline-containing peptides can be conjugated to drugs or other bioactive molecules to improve their targeting ability and reduce systemic toxicity, thus improving the efficacy and safety profiles of therapeutic agents.

N3-L-Cit-OH is also utilized in the creation of peptide-based vaccines and therapeutic agents. Citrulline, due to its role in immune modulation and its ability to alter protein folding, is an attractive target for developing peptides that can interact with immune cells. The incorporation of N3-L-Cit-OH into peptide vaccines could enhance immune system activation and provide a more robust immune response. This has potential applications in the development of vaccines for autoimmune diseases, cancer immunotherapy, and other conditions requiring immune system modulation.

Furthermore, N3-L-Cit-OH is valuable in the design of cyclic peptides and peptide mimetics. The incorporation of citrulline allows for greater flexibility in peptide structure, facilitating the formation of cyclic peptides that are more stable and resistant to proteolysis. These cyclic peptides are crucial in drug discovery as they can target specific proteins, enzymes, or receptors with higher specificity and affinity, which is especially useful in oncology, neurodegenerative diseases, and infectious diseases.

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

Historical Records: N3-L-Cit-OH
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