N-α-(9-Fluorenylmethoxycarbonyl)-S-(4-methoxybenzyl)-D-cysteine
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N-α-(9-Fluorenylmethoxycarbonyl)-S-(4-methoxybenzyl)-D-cysteine

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category
Fmoc-Amino Acids
Catalog number
BAT-005476
CAS number
200354-43-4
Molecular Formula
C26H25NO5S
Molecular Weight
463.55
N-α-(9-Fluorenylmethoxycarbonyl)-S-(4-methoxybenzyl)-D-cysteine
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(4-methoxyphenyl)methylsulfanyl]propanoic acid
Synonyms
Fmoc-D-Cys(MeOBzl)-OH; (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(4-methoxyphenyl)methylsulfanyl]propanoic acid; Fmoc-S-4-methoxybenzyl-D-cysteine; Fmoc-Cys(Mob)-OH
Purity
99%
Storage
Store at RT
InChI
InChI=1S/C26H25NO5S/c1-31-18-12-10-17(11-13-18)15-33-16-24(25(28)29)27-26(30)32-14-23-21-8-4-2-6-19(21)20-7-3-5-9-22(20)23/h2-13,23-24H,14-16H2,1H3,(H,27,30)(H,28,29)/t24-/m1/s1
InChI Key
IWZGYHFOLFRYPK-XMMPIXPASA-N
Canonical SMILES
COC1=CC=C(C=C1)CSCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

N-α-(9-Fluorenylmethoxycarbonyl)-S-(4-methoxybenzyl)-D-cysteine (Fmoc-MBzl-D-Cys) is a pivotal derivative of cysteine utilized in peptide synthesis. Here are four key applications of Fmoc-MBzl-D-Cys:

Peptide Synthesis: Embedded in the realm of solid-phase peptide synthesis (SPPS), Fmoc-MBzl-D-Cys stands as a cornerstone for integrating cysteine residues adorned with specific protective groups. This derivative enables targeted deprotection and coupling reactions, facilitating the intricate synthesis of multifaceted peptides. Its utility shines brightest in crafting peptides housing multiple disulfide bridges and intricate three-dimensional architectures.

Pharmaceutical Development: Within the sphere of peptide-based therapeutic advancements, Fmoc-MBzl-D-Cys assumes a pivotal role in chaperoning the synthesis of potential drug candidates. By shielding the thiol group, it safeguards the integrity of cysteine residues throughout synthesis, preserving them for the subsequent formation of crucial disulfide bonds. This preservation is indispensable for ensuring the stability and efficacy of therapeutic peptides, particularly those harnessed in cancer treatments and hormone therapies.

Structural Biology: Unveiling its prowess in the synthesis of peptides earmarked for structural inquiries like X-ray crystallography and NMR spectroscopy, Fmoc-MBzl-D-Cys emerges as a potent tool. Harnessing this derivative empowers researchers to procure well-defined peptides imprinted with specific modifications, laying the groundwork for comprehending protein folding interactions and functional nuances at a molecular scale.

Bioconjugation: Serving as a linchpin in the realm of bioconjugation, Fmoc-MBzl-D-Cys spearheads the creation of molecular unions where peptides intertwine with diverse entities such as drugs, proteins, or nanoparticles. The protective guise donned by cysteine expedites selective modifications and coupling reactions, enabling the tailored creation of targeted drug delivery systems, cutting-edge diagnostic tools, and innovative biomaterial constructs.

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