Fmoc-D-Cys(PhAcm)-OH

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Cat Number

INT1565818554

CAS Number

1565818-55-4

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Product Detail Description Customer Q&A

CAS Number

1565818-55-4

Synonyms

D-Cysteine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-S-[[(2-phenylacetyl)amino]methyl]-;N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-S-((2-phenylacetamido)methyl)-D-cysteine;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-S-[[(2-phenylacetyl)amino]methyl]-D-cysteine

Molecular Formula

C27H26N2O5S

Molecular Weight

490.57

Smiles

C1=CC=C(C=C1)CC(=O)NCSC[C@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Boiling Point

782.7℃

Relative Density

1.32

pKa

3.41

General Description

Fmoc-D-Cys(PhAcm)-OH is a selectively protected D-cysteine derivative where the thiol group is shielded by a phenylacetamidomethyl (PhAcm) group. This orthogonal protection strategy is essential for complex peptide synthesis.

Mechanism of Action

It acts as a specialized building block in solid-phase peptide synthesis (SPPS). The PhAcm group is stable to standard Fmoc deprotection and TFA cleavage conditions but can be specifically removed to allow for site-specific disulfide bond formation.

Application

It is primarily used in the synthesis of constrained cyclic peptides and therapeutic proteins where precise control over cysteine oxidation and folding is required.