N-α-(9-Fluorenylmethoxycarbonyl)-S-(4-methylbenzyl)-L-homocysteine
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N-α-(9-Fluorenylmethoxycarbonyl)-S-(4-methylbenzyl)-L-homocysteine

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Category
Fmoc-Amino Acids
Catalog number
BAT-001797
CAS number
1821768-91-5
Molecular Formula
C27H27NO4S
Molecular Weight
461.58
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[(4-methylphenyl)methylsulfanyl]butanoic acid
Synonyms
Fmoc-homoCys(CH3Bzl)-OH; Fmoc-Hcy(CH3Bzl)-OH; N-alpha-(9-Fluorenylmethoxycarbonyl)-S-(4-methylbenzyl)-L-homocysteine
Storage
Store at 2-8 °C
InChI
InChI=1S/C27H27NO4S/c1-18-10-12-19(13-11-18)17-33-15-14-25(26(29)30)28-27(31)32-16-24-22-8-4-2-6-20(22)21-7-3-5-9-23(21)24/h2-13,24-25H,14-17H2,1H3,(H,28,31)(H,29,30)/t25-/m0/s1
InChI Key
QKGHBNRSVICJRZ-VWLOTQADSA-N
Canonical SMILES
CC1=CC=C(C=C1)CSCCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

N-α-(9-Fluorenylmethoxycarbonyl)-S-(4-methylbenzyl)-L-homocysteine, also recognized as Fmoc-hcys(4mb)-OH, stands as a specialized amino acid derivative with diverse applications in peptide synthesis and biochemical exploration.

Peptide Synthesis: Within the realm of solid-phase peptide synthesis, Fmoc-hcys(4mb)-OH plays a pivotal role in introducing homocysteine residues adorned with protective groups. This derivative facilitates the methodical construction of intricate peptides, ensuring the preservation of functional groups throughout various stages. Its significance is paramount in crafting peptides tailored for pharmaceutical and investigative objectives.

Protein Engineering: Positioned at the nexus of protein engineering, Fmoc-hcys(4mb)-OH proves instrumental in embedding homocysteine within proteins to delve into their structural and functional nuances. The presence of homocysteine allows for tailored modifications, like disulfide bond formation, augmenting the stability and functionality of proteins. This application holds intrinsic value in sculpting novel proteins and therapeutic modalities.

Bioconjugation: Serving as a foundational block in the evolution of bioconjugates, Fmoc-hcys(4mb)-OH facilitates the linkage of peptides to diverse molecules, such as drugs, imaging agents, or polymers. The shielded homocysteine residue offers a reactive platform for subsequent conjugation processes. This methodology finds extensive utilization in precision-targeted drug delivery systems and diagnostic apparatuses.

Chemical Biology: Positioned at the forefront of chemical biology research, Fmoc-hcys(4mb)-OH is harnessed to explore protein-protein and protein-ligand interactions. By integrating this derivative into peptides, researchers can probe the repercussions of specific amino acid modifications on biological functions. This inquiry aids in unraveling molecular mechanisms and pinpointing fresh therapeutic targets within intricate biological systems.

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