N-Fmoc-S-(4-methoxybenzyl)-L-cysteine, CAS No. 141892-41-3

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141892-41-3

Catalog No. EBD28416

CAS 141892-41-3

Name N-Fmoc-S-(4-methoxybenzyl)-L-cysteine

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Basic Information

Synonyms: n-alpha-(9-fluorenylmethoxycarbonyl)-s-p-methoxybenzyl-l-cysteine n-alpha-(9-fluorenylmethyloxycarbonyl)-s-(4-methoxybenzyl)-l-cysteine n-alpha-fmoc-s-(4-methoxybenzyl)-l-cysteine n-alpha-fmoc-s-p-methoxybenzyl-l-cysteine fmoc-s-4-methoxybenzyl-l-cysteine fmoc-s-p-methoxybenzyl-l-cysteine fmoc-cys(pmeobzl)-oh N-(9-Fluorenylmethyloxycarbonyl)-S-(4-methoxybenzyl)-L-cysteine Fmoc-Cys(Mob)-OH N-Fmoc-S-(4-methoxybenzyl)-L-cysteine N(alpha)-fmoc-S-(4-methoxybenzyl)-L-cysteine Fmoc-Cys(4-MeO-Bzl)-OH N-[(9H-fluoren-9-ylmethoxy)carbonyl]-S-(4-methoxybenzyl)-L-cysteine

Molecular Formula: C26H25NO5S

Molecular Weight: 463.55

MDL Number: MFCD00065635

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Peptides and Peptidomimetics

Product Description:

N-Fmoc-S-(4-methoxybenzyl)-L-cysteine is a protected derivative of the amino acid L-cysteine. It features two key protective groups: the N-terminal Fmoc (9-fluorenylmethoxycarbonyl) group, which is acid-stable but base-labile, and the S-(4-methoxybenzyl) (Mob) group, which protects the thiol side chain of cysteine. This compound is a white to off-white crystalline powder. This derivative is a crucial building block in solid-phase peptide synthesis (SPPS), specifically using the Fmoc/t-Bu strategy. The Fmoc group is the standard N-protecting group for this methodology, allowing for mild deprotection with piperidine. The S-Mob group is stable under the basic conditions used for Fmoc removal but can be cleaved under strong acidic conditions (e.g., with trifluoroacetic acid) during the final global deprotection step. It is primarily used for the controlled incorporation of cysteine residues into synthetic peptides, enabling the subsequent formation of disulfide bonds or other modifications via the free thiol. As a specialty amino acid derivative, it is not a general-purpose reagent but a dedicated tool for peptide chemistry. Its primary value lies in enabling the synthesis of complex peptides and proteins containing cysteine, which are of significant interest in pharmaceutical research, biochemistry, and the development of peptide-based therapeutics and diagnostics.

Physical Properties

Melting Point: ~140 °C

Boiling Point: 689.5 °C at 760 mmHg

Flash Point: 370.8 °C

Density: 1.295 g/cm3

Storage: 2-8°C