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(R)-2-((tert-Butoxycarbonyl)amino)-3-mercapto-3-methylbutanoic acid

  • CAS No. 110763-40-1

  • Cat. No. CS-0196504
  • Purity≥97%
  • MDL No.None

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

(R)-2-((tert-Butoxycarbonyl)amino)-3-mercapto-3-methylbutanoic acid|CS-0196504

Structure of 110763-40-1

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General Information

  • CAS No. 110763-40-1
  • Cat. No. CS-0196504
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₉NO₄S
  • Molecular Weight 249.33
  • Synonym(s) N-tert-Butoxycarbonyl-3-mercapto-L-valine
  • SMILES CC(C)(OC(N[C@@H](C(C)(S)C)C(O)=O)=O)C

Description

This chiral thiol-containing amino acid derivative features a protected amine and a reactive sulfhydryl group, enabling selective conjugation in peptide synthesis. The tert-butyl carbamate moiety ensures stability during handling and purification, while the mercapto functionality facilitates site-specific labeling or disulfide bridge formation in bioconjugation workflows.

Application

(R)-2-((tert-Butoxycarbonyl)amino)-3-mercapto-3-methylbutanoic acid serves as a versatile chiral building block for the synthesis of cysteine-derived peptidomimetics and thioether-containing heterocycles. The protected amine and free thiol functionalities enable orthogonal transformations, while the tert-butyl carbamate group provides bench stability and facile deprotection under mild acidic conditions. This scaffold is well-suited for solid-phase synthesis and conjugation chemistry in medicinal chemistry campaigns.

Synthesis

  • Route1

    References

    • WO2013/192286 A1, ; Paragraph 00234 ;
  • Route2

    References

    • Journal of Organic Chemistry, , vol. 65, # 10 p. 3010 - 3017

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07,GHS08,GHS09
Signal Word : Danger
UN#: 3077
Class : 9
Packing Group : Ⅲ
Hazard Statements : H315-H319-H372-H413
Precautionary Statements : P264-P273-P280-P302+P352-P362+P364-P501

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Computational Chemistry Data

  • TPSA   75.63
  • LogP   1.6727
  • H_Acceptors   4
  • H_Donors   3
  • Rotatable_Bonds   3

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