S-(Acetamidomethyl)-N-(tert-butoxycarbonyl)-L-cysteine, CAS No. 19746-37-3

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19746-37-3

Catalog No. EBD18160

CAS 19746-37-3

Name S-(Acetamidomethyl)-N-(tert-butoxycarbonyl)-L-cysteine

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Basic Information

Synonyms: 1,2-Epoxy-cis-cyclooct-5-ene 5,6-Epoxy-cis-cyclooctene 5,6-Epoxycyclooctene S-(Acetamidomethyl)-N-(tert-butoxycarbonyl)-L-cysteine boc-S-acetaminomethyl-L-cysteine N-T-boc-S-acetamidomethyl-L-cysteine Boc-Cys(Acm)-OH S-[(acetylamino)methyl]-N-(tert-butoxycarbonyl)-L-cysteine S-[(acetylamino)methyl]-N-(tert-butoxycarbonyl)-D-cysteine

Molecular Formula: C11H20N2O5S

Molecular Weight: 292.35

MDL Number: MFCD00038252

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks Medicinal Chemistry > Biochemicals and Life Science Reagents > Peptides and Peptidomimetics

Product Description:

S-Acetamidomethyl-N-tert-butoxycarbonyl-L-cysteine is a protected cysteine derivative. Its structure features both an N-terminal tert-butoxycarbonyl (Boc) protecting group and an S-acetamidomethyl (Acm) protecting group on the thiol side chain of cysteine. This dual protection strategy is crucial in peptide synthesis. This compound serves as a key building block in solid-phase and solution-phase peptide synthesis. The Boc group protects the amino functionality during chain assembly and can be removed under acidic conditions without affecting the Acm group. The Acm group is a widely used thiol-protecting group that is stable to the acidic conditions used for Boc removal and to hydrogenolysis, but can be selectively removed by treatment with iodine or mercury(II) salts. This allows for the controlled formation of disulfide bonds in the synthesis of peptides containing cysteine bridges, such as oxytocin, somatostatin, and various other bioactive peptides and proteins. The product is a high-purity reagent specifically designed for research and development in peptide chemistry and pharmaceutical manufacturing. Proper handling requires standard laboratory safety precautions for fine chemicals.

Physical Properties

Melting Point: 111-114 °C

Boiling Point: 531.5 °C at 760mmHg

Flash Point: 275.2 °C

Density: 1.231 g/cm3

Storage: −20°C