Boc-Cys(Acm)-OH

Boc-Cys(Acm)-OH is a fundamental building block in Boc-based solid-phase peptide synthesis (SPPS), enabling the controlled incorporation of cysteine residues into synthetic peptides. The unique value of Boc-Cys(Acm)-OH lies in its orthogonal protection strategy: the Boc group protects the α-amino group during chain assembly and is cleaved by TFA, while the Acm group protects the thiol side chain and remains intact under these acidic conditions. This orthogonality allows Boc-Cys(Acm)-OH to be used in the synthesis of complex peptides containing multiple cysteine residues, where the Acm group can be selectively removed at a later stage (typically by iodine or mercury(II) acetate) to enable controlled disulfide bond formation. Boc-Cys(Acm)-OH has been employed in the synthesis of natriuretic peptides, oxytocin, and other bioactive peptides. The compound presents as a white to off-white crystalline powder with a melting point of 111–114 °C and a specific rotation of [α]²⁰/D −36.5 ± 1.5° (c = 1% in H₂O). For researchers engaged in the chemical synthesis of cysteine-rich peptides and proteins, Boc-Cys(Acm)-OH provides the protection and selectivity essential for achieving high-quality synthetic products.


Product Parameters

FAQ

Q2: Why is the Acm group important?
A: The Acm group on Boc-Cys(Acm)-OH is orthogonal to acidic Boc deprotection conditions, remaining intact during chain assembly. This allows the thiol to be protected throughout peptide synthesis and selectively deprotected later for controlled disulfide bond formation.

Storage Conditions

Shelf life: Long-term stability is maintained when stored at 2–8 °C in a dry, sealed container. For extended storage, ensure the container is tightly sealed to prevent moisture ingress.

Handling precautions: Use in a fume hood. Wear chemical-resistant gloves, safety goggles, and a lab coat. Avoid generating dust. After handling, wash hands thoroughly. Refer to the Safety Data Sheet (SDS) for complete safety information.

Application Scenarios

Boc SPPS of Cysteine-Containing Peptides

Boc-Cys(Acm)-OH is a fundamental building block for Boc-based solid-phase peptide synthesis, enabling the incorporation of cysteine residues into synthetic peptides.

Controlled Disulfide Bond Formation

The Acm group on Boc-Cys(Acm)-OH enables selective deprotection and controlled formation of disulfide bonds in peptides containing multiple cysteine residues. This is essential for the synthesis of biologically active peptides with defined disulfide connectivity.

Natriuretic Peptide Synthesis
Boc-Cys(Acm)-OH has been employed in the synthesis of natriuretic peptides, including brain natriuretic peptide (BNP).

Oxytocin Synthesis
Boc-Cys(Acm)-OH is used as a building block in the synthesis of oxytocin, a peptide hormone with diverse physiological functions.

Bioactive Peptide Research
Boc-Cys(Acm)-OH enables the synthesis of cysteine-rich bioactive peptides for studying structure-activity relationships, receptor interactions, and therapeutic potential.

Peptide Drug Development
Pharmaceutical researchers use Boc-Cys(Acm)-OH in the development of peptide-based therapeutics where precise control over cysteine incorporation and disulfide bond formation is required.

Process Development & Scale-Up
Peptide chemists use Boc-Cys(Acm)-OH for reaction optimization, coupling condition screening, and development of scalable SPPS processes.

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