Boc-S-4-methylbenzyl-L-homocysteine
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Boc-S-4-methylbenzyl-L-homocysteine

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Category
BOC-Amino Acids
Catalog number
BAT-007165
CAS number
201419-15-0
Molecular Formula
C17H25NO4S
Molecular Weight
339.45
Boc-S-4-methylbenzyl-L-homocysteine
IUPAC Name
(2S)-4-[(4-methylphenyl)methylsulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
Synonyms
Boc-L-HomoCys(pMeBzl)-OH
Related CAS
214630-13-4 (D-isomer)
Appearance
White solid
Purity
≥ 99% (HPLC)
Melting Point
84-89 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C17H25NO4S/c1-12-5-7-13(8-6-12)11-23-10-9-14(15(19)20)18-16(21)22-17(2,3)4/h5-8,14H,9-11H2,1-4H3,(H,18,21)(H,19,20)/t14-/m0/s1
InChI Key
LIUGCVMBJYHYNA-AWEZNQCLSA-N
Canonical SMILES
CC1=CC=C(C=C1)CSCCC(C(=O)O)NC(=O)OC(C)(C)C

Boc-S-4-methylbenzyl-L-homocysteine is a chemical compound used in various biochemical and medicinal research applications. Here are some key applications of Boc-S-4-methylbenzyl-L-homocysteine:

Peptide Synthesis: Boc-S-4-methylbenzyl-L-homocysteine is extensively used as a protected amino acid in solid-phase peptide synthesis. The Boc (tert-butyloxycarbonyl) group serves as a protecting group for the amino function, preventing unwanted side reactions during peptide chain elongation. This enables the synthesis of highly specific and functional peptides for drug development and biochemical studies.

Enzyme Inhibition Studies: Researchers utilize Boc-S-4-methylbenzyl-L-homocysteine to investigate enzyme inhibition mechanisms, particularly in the context of sulfur-containing amino acid metabolism. By incorporating this compound into enzyme assays, scientists can observe its effects on enzyme activity and kinetics. This helps in identifying potential inhibitors for therapeutic targets in diseases such as cancer and cardiovascular disorders.

Structural Biology: In structural biology, Boc-S-4-methylbenzyl-L-homocysteine is used to synthesize modified peptides for crystallographic studies. The presence of the 4-methylbenzyl group enhances the hydrophobic interactions within the peptide, aiding in crystal formation. This facilitates the determination of high-resolution protein structures, providing insights into protein function and interactions.

Bioconjugation: Boc-S-4-methylbenzyl-L-homocysteine can be employed in bioconjugation techniques for labeling and detecting biomolecules. The homocysteine moiety allows for the introduction of thiol groups, which can readily react with maleimide or other thiol-reactive reagents. This enables the conjugation of peptides or proteins to fluorescent dyes, affinity tags, or other functional groups for various analytical and diagnostic applications.

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