Fmoc-S-tert-butoxycarbonylmethyl-L-cysteine
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Fmoc-S-tert-butoxycarbonylmethyl-L-cysteine

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Category
Fmoc-Amino Acids
Catalog number
BAT-003835
CAS number
269730-62-3
Molecular Formula
C24H27NO6S
Molecular Weight
457.55
Fmoc-S-tert-butoxycarbonylmethyl-L-cysteine
IUPAC Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]sulfanylpropanoic acid
Synonyms
Fmoc-L-Cys(τ-butoxycarbonylmethyl)-OH; Fmoc-Cys(Boc-methyl)-OH; (R)-Fmoc-2-amino-3-(tert-butoxycarbonylmethylsulfanyl)-propionic acid; Fmoc-Cys(t-butylcarboxymethyl)-OH; Fmoc-Cys(tert-butoxycarbonylmethyl)-OH
Appearance
Syrup to White solid
Purity
≥ 97% (HPLC)
Density
1.273±0.06 g/cm3
Boiling Point
645.8±55.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C24H27NO6S/c1-24(2,3)31-21(26)14-32-13-20(22(27)28)25-23(29)30-12-19-17-10-6-4-8-15(17)16-9-5-7-11-18(16)19/h4-11,19-20H,12-14H2,1-3H3,(H,25,29)(H,27,28)/t20-/m0/s1
InChI Key
NLQIBSKINOPHNA-FQEVSTJZSA-N
Canonical SMILES
CC(C)(C)OC(=O)CSCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Fmoc-S-tert-butoxycarbonylmethyl-L-cysteine, a derivative utilized in peptide synthesis, plays a critical role in protecting and ensuring the precise formation of peptides. Here are four key applications of Fmoc-S-tert-butoxycarbonylmethyl-L-cysteine:

Peptide Synthesis: Integral to solid-phase peptide synthesis, Fmoc-S-tert-butoxycarbonylmethyl-L-cysteine safeguards the thiol group in cysteine residues, selectively guiding the formation of specific disulfide bonds that dictate the correct folding of peptides. The protective group can be gently removed under mild conditions, preserving the structural integrity of the peptide chain amidst its intricate assembly process.

Pharmaceutical Development: In the realm of drug development, this compound serves to create peptide-based therapeutic candidates, enhancing their stability and efficacy. By shielding cysteine residues throughout synthesis, researchers ensure that the resulting therapeutic peptides maintain their intended structure and biological function, paving the way for the production of more potent and reliable peptide-based treatments.

Protein Engineering: Fmoc-S-tert-butoxycarbonylmethyl-L-cysteine facilitates the precise integration of modified cysteine residues into proteins, enabling the study of protein structure and function or the design of proteins with novel characteristics. This technique is invaluable for crafting proteins with potential industrial or medicinal applications, driving innovation in protein engineering for various sectors.

Bioconjugation Strategies: Leveraging this compound streamlines the creation of cysteine-modified peptides for bioconjugation purposes, allowing for the strategic attachment of peptides to diverse molecules such as fluorophores, drugs, or nanoparticles. By incorporating protected cysteine residues in a targeted manner, researchers can develop advanced diagnostic tools, tailored drug delivery systems, and other biotechnological applications with enhanced precision and functionality.

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