Fmoc-(2R,4R)-4-azidoproline - CAS 1378847-51-8

Fmoc-(2R,4R)-4-azidoproline - CAS 1378847-51-8 Catalog number: BADC-01967

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Category
ADCs Linker
Product Name
Fmoc-(2R,4R)-4-azidoproline
CAS
1378847-51-8
Catalog Number
BADC-01967
Molecular Formula
C20H18N4O4
Molecular Weight
378.40

Ordering Information

Catalog Number Size Price Quantity
BADC-01967 -- $--
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Synonyms
Fmoc-Pro(4-N3) (2R,4R); (2R,4R)-4-Azido-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid
IUPAC Name
(2R,4R)-4-azido-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid
Canonical SMILES
C1C(CN(C1C(=O)O)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)N=[N+]=[N-]
InChI
InChI=1S/C20H18N4O4/c21-23-22-12-9-18(19(25)26)24(10-12)20(27)28-11-17-15-7-3-1-5-13(15)14-6-2-4-8-16(14)17/h1-8,12,17-18H,9-11H2,(H,25,26)/t12-,18-/m1/s1
InChIKey
HOPXMBBEYJTPNX-KZULUSFZSA-N
Melting Point
177-180°C
Appearance
White crystalline powder
Purity
≥ 99% (HPLC, Assay by titration)
Storage
Store at 2-8 °C

Fmoc-(2R4R)-4-azidoproline, a versatile chemical compound, finds extensive utility in peptide synthesis and bioconjugation. Here are four key applications of Fmoc-(2R4R)-4-azidoproline:

Peptide Synthesis: Integral to synthetic peptides, Fmoc-(2R4R)-4-azidoproline boasts a distinct azide functional group, facilitating site-specific modifications through click chemistry. Researchers utilize this compound to craft modified peptides with augmented stability or bioactivity, crucial for advancements in drug development and protein engineering.

Bioconjugation: Harnessing the reactive azide group in Fmoc-(2R4R)-4-azidoproline, researchers engage in the highly efficient Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction with alkyne-containing molecules. This process enables precise conjugation of diverse biomolecules like fluorophores, drugs, or imaging agents to peptides or proteins, fostering the development of targeted therapeutics and diagnostic tools.

Structural Biology: By incorporating Fmoc-(2R4R)-4-azidoproline into proteins, researchers gain the ability to introduce controlled structural modifications. Through selective protein modification or cross-linking, scientists delve into protein folding, stability, and interactions with other biomolecules, offering insights into protein structure-function relationships and facilitating the design of stable protein constructs for therapeutic purposes.

Chemical Biology: In the realm of chemical biology, Fmoc-(2R4R)-4-azidoproline serves as a pivotal component in designing chemical probes for investigating biological systems. Chemical probes containing this azide proline can label, track, or inhibit specific biomolecules within cellular environments, aiding in the mapping of cellular pathways, identification of interaction networks, and discovery of potential drug targets.

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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