Fmoc-S-trityl-L-homocysteine
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Fmoc-S-trityl-L-homocysteine

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Category
Fmoc-Amino Acids
Catalog number
BAT-007491
CAS number
167015-23-8
Molecular Formula
C38H33NO4S
Molecular Weight
599.74
Fmoc-S-trityl-L-homocysteine
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-tritylsulfanylbutanoic acid
Synonyms
Fmoc-L-HomoCys(Trt)-OH; (S)-2-(Fmoc-amino)-4-tritylsulfanyl-butyric acid
Appearance
White to yellow powder
Purity
≥ 97% (HPLC)
Melting Point
74-115 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C38H33NO4S/c40-36(41)35(39-37(42)43-26-34-32-22-12-10-20-30(32)31-21-11-13-23-33(31)34)24-25-44-38(27-14-4-1-5-15-27,28-16-6-2-7-17-28)29-18-8-3-9-19-29/h1-23,34-35H,24-26H2,(H,39,42)(H,40,41)/t35-/m0/s1
InChI Key
FKBGJLDYRSFHBT-DHUJRADRSA-N
Canonical SMILES
C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)SCCC(C(=O)O)NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46

Fmoc-S-trityl-L-homocysteine, a protective form of homocysteine widely employed in peptide synthesis and diverse biochemical applications, offers a myriad of uses. Here are four key applications:

Peptide Synthesis: The utility of Fmoc-S-trityl-L-homocysteine shines in the realm of solid-phase peptide synthesis. Its protective groups shield the homocysteine side chain from reactivity throughout the peptide assembly process. Upon completion of synthesis, selective conditions can strip away the protective groups, unveiling the liberated homocysteine nestled within the peptide chain.

Chemical Biology Research: Enter the world of post-translational modifications and protein structure-function relationships, where Fmoc-S-trityl-L-homocysteine plays a pivotal role. By introducing homocysteine into peptides and proteins, researchers delve into the significance of sulfur-containing amino acids in biological processes. This exploration is key to unraveling the intricacies of protein folding, enzyme functionalities, and interaction networks.

Pharmaceutical Development: Embark on a journey into drug discovery, where Fmoc-S-trityl-L-homocysteine contributes to the development of groundbreaking peptide-based therapeutics. Homocysteine residues emerge as linchpins for peptides targeting specific receptors or enzymes. Incorporating homocysteine-laden peptides amplifies binding affinity and specificity, paving the way for more potent drug candidates and innovative therapeutic solutions.

Bioconjugation Studies: Amid bioconjugation applications, Fmoc-S-trityl-L-homocysteine takes center stage in facilitating the coupling of synthetic peptides with various molecules, from fluorescent tags to toxins. The trityl-protected homocysteine orchestrates targeted binding and stable linkage formation, all while warding off undesired side reactions. This methodology proves invaluable in crafting molecular probes tailored for imaging techniques and precision-targeted therapies.

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