Fmoc-S-tert-butylthio-D-cysteine
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Fmoc-S-tert-butylthio-D-cysteine

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Category
Fmoc-Amino Acids
Catalog number
BAT-003838
CAS number
501326-55-2
Molecular Formula
C22H25NO4S2
Molecular Weight
431.60
Fmoc-S-tert-butylthio-D-cysteine
IUPAC Name
(2S)-3-(tert-butyldisulfanyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
Fmoc-D-Cys(StBu)-OH; (2R)-3-tert-butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Appearance
White to off-white powder
Purity
≥ 98% (HPLC)
Density
1.281±0.06 g/cm3
Melting Point
66-77 °C
Boiling Point
623.0±55.0 °C
Storage
Store at -20 °C
InChI
InChI=1S/C22H25NO4S2/c1-22(2,3)29-28-13-19(20(24)25)23-21(26)27-12-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h4-11,18-19H,12-13H2,1-3H3,(H,23,26)(H,24,25)/t19-/m1/s1
InChI Key
ZDUMTHLUTJOUML-LJQANCHMSA-N
Canonical SMILES
CC(C)(C)SSCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Fmoc-S-tert-butylthio-D-cysteine, a specialized amino acid derivative, plays a pivotal role in peptide synthesis and biochemical research. Here are four key applications of Fmoc-S-tert-butylthio-D-cysteine:

Peptide Synthesis: In the realm of solid-phase peptide synthesis, Fmoc-S-tert-butylthio-D-cysteine emerges as a vital component for incorporating cysteine residues with tailored protective groups into peptides. This precision enables exact control over disulfide bond formation, a critical aspect for crafting peptides with accurate three-dimensional structures. Such peptides find utility in therapeutic advancements and profound structural biology explorations.

Proteomics Research: Within the dynamic field of proteomics, Fmoc-S-tert-butylthio-D-cysteine serves as a versatile tool for synthesizing labeled peptides essential for mass spectrometry-based investigations. The thio-protective group allows for selective cleavage and labeling, facilitating the intricate analysis of complex protein mixtures and post-translational modifications. This aids in unraveling intricate protein interactions and identifying key disease biomarkers.

Drug Design: Integration of Fmoc-S-tert-butylthio-D-cysteine into peptide-based drug candidates offers researchers a glimpse into the impact of cysteine residues on drug stability and functionality. The tert-butylthio group offers crucial protection during synthesis, ensuring the functional integrity of the cysteine side chain. This is particularly pertinent for designing peptide drugs enriched with cysteine, targeted towards specific disease pathways, opening new avenues for therapeutic breakthroughs.

Biomaterial Development: When it comes to biomaterial innovation, Fmoc-S-tert-butylthio-D-cysteine proves invaluable for crafting cysteine-containing peptides that lay the foundation for novel biomaterials. These peptides have the ability to form hydrogels or other intricate nanostructures through disulfide crosslinking, facilitating the creation of biocompatible materials. Such materials hold promise for diverse applications in tissue engineering, drug delivery systems, and the realm of regenerative medicine, pushing the boundaries of scientific possibilities.

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