Fmoc-Cys(STmp)-OH
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Fmoc-Cys(STmp)-OH

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Category
Fmoc-Amino Acids
Catalog number
BAT-008417
CAS number
1403834-74-1
Molecular Formula
C27H27NO7S2
Molecular Weight
541.6
IUPAC Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2,4,6-trimethoxyphenyl)disulfanyl]propanoic acid
InChI
InChI=1S/C27H27NO7S2/c1-32-16-12-23(33-2)25(24(13-16)34-3)37-36-15-22(26(29)30)28-27(31)35-14-21-19-10-6-4-8-17(19)18-9-5-7-11-20(18)21/h4-13,21-22H,14-15H2,1-3H3,(H,28,31)(H,29,30)/t22-/m0/s1
InChI Key
GADCBXMSWHDNAU-QFIPXVFZSA-N
Canonical SMILES
COC1=CC(=C(C(=C1)OC)SSCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)OC

Fmoc-Cys(STmp)-OH, a protected amino acid integral to peptide synthesis and biotechnology, finds diverse applications. Here are four key uses:

Solid-Phase Peptide Synthesis (SPPS): Widely utilized in SPPS, Fmoc-Cys(STmp)-OH plays a crucial role in the stepwise assembly of peptides on a solid matrix. The STmp protecting group shields the thiol moiety of cysteine, safeguarding it from unintended reactions during peptide construction. This approach facilitates the precise and efficient synthesis of peptides with accurate sequences and functionalities, advancing peptide chemistry.

Peptide Therapeutics Development: In the realm of peptide-based drug development, Fmoc-Cys(STmp)-OH is indispensable for incorporating cysteine residues, crucial for forming disulfide bonds. These bonds are vital for the stability and bioactivity of therapeutic peptides. By harnessing this protected form of cysteine, researchers can regulate the formation of disulfide linkages, resulting in the production of more potent and enduring therapeutic peptides, enhancing treatment efficacy.

Protein Engineering: Employed in protein engineering endeavors, Fmoc-Cys(STmp)-OH facilitates the generation of modified proteins featuring cysteine residues at specific sites. This enables the introduction of post-translational modifications, bioconjugation sites, or the reinforcement of protein structures via disulfide bridges. Engineered proteins endowed with enhanced functionalities or stability offer profound benefits for both research and therapeutic applications, driving innovation in the field of protein science.

Bioconjugation Techniques: A key player in bioconjugation, Fmoc-Cys(STmp)-OH enables the precise attachment of diverse biochemical entities to peptides or proteins via the cysteine thiol group. The protected cysteine permits selective and controlled conjugation reactions, encompassing fluorescent labeling, drug attachment, or surface immobilization. This capability is instrumental in crafting biomolecular tools and diagnostic assays, expanding the horizon of bioconjugation technologies and applications.

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