Boc-S-acetamidomethyl-L-cysteine
Need Assistance?
  • US & Canada:
    +
  • UK: +

Boc-S-acetamidomethyl-L-cysteine

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

Category
BOC-Amino Acids
Catalog number
BAT-002889
CAS number
19746-37-3
Molecular Formula
C11H20N2O5S
Molecular Weight
292.30
Boc-S-acetamidomethyl-L-cysteine
IUPAC Name
(2R)-3-(acetamidomethylsulfanyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-L-Cys(Acm)-OH; (R)-3-(Acetylamino-methylsulfanyl)-2-tert-butoxycarbonylamino-propionic acid; S-(Acetamidomethyl)-N-(tert-butoxycarbonyl)-L-cysteine
Appearance
White powder
Purity
≥ 98% (HPLC)
Density
1.231±0.06 g/cm3(Predicted)
Melting Point
103-117 °C
Boiling Point
531.5±50.0 °C(Predicted)
Storage
Store at 2-8°C
InChI
InChI=1S/C11H20N2O5S/c1-7(14)12-6-19-5-8(9(15)16)13-10(17)18-11(2,3)4/h8H,5-6H2,1-4H3,(H,12,14)(H,13,17)(H,15,16)/t8-/m0/s1
InChI Key
HLCTYBOTPCIHTG-QMMMGPOBSA-N
Canonical SMILES
CC(=O)NCSCC(C(=O)O)NC(=O)OC(C)(C)C

Boc-S-acetamidomethyl-L-cysteine, a versatile derivative employed in peptide synthesis and various biochemical applications, finds widespread utility in several key areas.

Peptide Synthesis: Serving as a fundamental building block in peptide synthesis, Boc-S-acetamidomethyl-L-cysteine stands out for its integration capabilities enabled by the Boc (tert-butyloxycarbonyl) protective group. This compound facilitates the systematic construction of peptides through solid-phase peptide synthesis, particularly enabling the inclusion of cysteine residues. These residues play a critical role in establishing disulfide bridges, crucial for stabilizing peptide structures, showcasing the intricate dance of chemical bonds in peptide formation.

Protein Engineering: In the realm of protein engineering, Boc-S-acetamidomethyl-L-cysteine emerges as a powerful tool for strategically introducing cysteine residues at precise locations within protein sequences. This strategic maneuver empowers researchers to craft proteins with novel functionalities, such as heightened stability or unique binding properties. Moreover, this modification opens doors to the creation of prosthetic groups or the attachment of other chemical entities, setting the stage for advanced protein manipulations and investigations into the remarkable diversity of protein functions.

Bioconjugation: Delving into bioconjugation techniques, Boc-S-acetamidomethyl-L-cysteine shines as a pivotal anchor point for tethering diverse molecules to peptides and proteins. The thiol group of the cysteine residue acts as a linchpin for forming covalent bonds with reactive moieties, enabling the assembly of intricate biomolecular structures. This application plays a vital role in the development of targeted drug delivery systems and diagnostic tools, illustrating the intricate interplay between chemical bonds and molecular designs in bioengineering.

Chemical Biology: Within the domain of chemical biology, Boc-S-acetamidomethyl-L-cysteine serves as a key player in unraveling the functional significance of cysteine residues within natural proteins. By selectively introducing this derivative into proteins, researchers embark on a journey to explore the pivotal roles of cysteine in enzyme catalysis, redox reactions, and structural stability. This intricate study sheds light on the nuanced functionalities of proteins and serves as a springboard for designing novel biomolecules with enhanced functionalities, elucidating the intricate web of chemical interactions in biological systems.

Online Inquiry
Verification code
Inquiry Basket