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Dimethyl 4,4'-disulfanediyl(2S,2'S)-bis(2-((tert-butoxycarbonyl)amino)butanoate)

  • CAS No. 144373-70-6

  • Cat. No. CS-0158520
  • Purity≥97%
  • MDL No.MFCD31803853

*For research and further manufacturing use only, not for direct human use.

Dimethyl 4,4'-disulfanediyl(2S,2'S)-bis(2-((tert-butoxycarbonyl)amino)butanoate)|CS-0158520

Structure of 144373-70-6

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General Information

  • CAS No. 144373-70-6
  • Cat. No. CS-0158520
  • Purity ≥97%
  • MDL No. MFCD31803853
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₀H₃₆N₂O₈S₂
  • Molecular Weight 496.64
  • Synonym(s) N,N'-bis[(tert-butyloxy)carbonyl]-L-hoMocystine diMethyl ester
  • SMILES CC(C)(C)OC(N[C@H](C(OC)=O)CCSSCC[C@@H](C(OC)=O)NC(OC(C)(C)C)=O)=O

Description

Dimethyl 4,4'-disulfanediyl(2S,2'S)-bis(2-((tert-butoxycarbonyl)amino)butanoate features a disulfide-linked scaffold flanked by two protected amino acid ester moieties. This bifunctional reagent enables site-specific conjugation in peptide synthesis and protein modification workflows. The tert-butyl carbamate groups provide orthogonal protection, while the disulfide linkage offers redox-responsive cleavage under physiological conditions.

Application

Dimethyl 4,4'-disulfanediyl(2S,2'S)-bis(2-((tert-butoxycarbonyl)amino)butanoate serves as a stable, bench-ready disulfide-linked dipeptide building block for the synthesis of cysteine-containing peptides and thiol-based conjugates. Its tert-butoxycarbonyl (Boc) groups provide orthogonal protection, enabling selective deprotection during solid-phase or solution-phase peptide synthesis. The disulfide moiety facilitates controlled redox-dependent dimerization and is compatible with standard coupling protocols, offering reliable access to cyclic peptides and protein conjugates.

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P280-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   129.26
  • LogP   3.2806
  • H_Acceptors   10
  • H_Donors   2
  • Rotatable_Bonds   11

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