Fmoc-L-cysteine amide
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Fmoc-L-cysteine amide

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Category
Fmoc-Amino Acids
Catalog number
BAT-000415
CAS number
623177-62-8
Molecular Formula
C18H18N2O3S
Molecular Weight
342.40
IUPAC Name
9H-fluoren-9-ylmethyl N-[(2R)-1-amino-1-oxo-3-sulfanylpropan-2-yl]carbamate
Synonyms
Fmoc-L-Cys-NH2; Nα-Fmoc-L-cysteinamide; 9H-fluoren-9-ylmethyl N-[(2R)-1-amino-1-oxo-3-sulfanylpropan-2-yl]carbamate
Appearance
White to off-white powder
Storage
Store at 2-8 °C
InChI
InChI=1S/C18H18N2O3S/c19-17(21)16(10-24)20-18(22)23-9-15-13-7-3-1-5-11(13)12-6-2-4-8-14(12)15/h1-8,15-16,24H,9-10H2,(H2,19,21)(H,20,22)/t16-/m0/s1
InChI Key
QNQILYKUOWQTEZ-INIZCTEOSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CS)C(=O)N

Fmoc-L-cysteine amide, a versatile chemical compound, plays a crucial role in peptide synthesis and various biochemical applications. Here are four key applications of Fmoc-L-cysteine amide:

Solid-Phase Peptide Synthesis: Serving as a foundational element in solid-phase peptide synthesis (SPPS), Fmoc-L-cysteine amide is integral for incorporating cysteine residues into peptides, essential for the formation of disulfide bonds. These bonds significantly enhance the stability and functionality of numerous bioactive peptides and proteins, contributing to their diverse biological activities.

Protein Engineering: Within the realm of protein engineering, Fmoc-L-cysteine amide is harnessed to selectively introduce cysteine residues into proteins, facilitating site-specific labeling, cross-linking, or the formation of covalent modifications. By precisely manipulating proteins, researchers can probe structure-function relationships and engineer proteins with novel characteristics, pushing the boundaries of bioengineering possibilities.

Bioconjugation: In the domain of bioconjugation, Fmoc-L-cysteine amide is a linchpin in linking peptides or proteins to a spectrum of molecules, ranging from fluorescent dyes to drugs and nanoparticles. Through the thiol group present in cysteine, stable thioether bonds can be formed with maleimide-containing compounds, enabling the development of targeted therapeutics, diagnostic tools, and biosensors of unparalleled precision and efficacy.

Peptide Drug Development: In the arena of peptide drug development, Fmoc-L-cysteine amide shines as a cornerstone in synthesizing peptides endowed with specific biological activities. It facilitates the construction of peptides capable of mimicking protein interactions or inhibiting key enzymes, paving the way for the creation of innovative therapeutics targeting a diverse array of diseases, encompassing cancer, diabetes, and infectious maladies with unparalleled potency and specificity.

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