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CS-W001157 4
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3-(2-Thienyl)-D-alanine

  • CAS No. 62561-76-6

  • Cat. No. CS-M2655
  • Purity≥98%
  • MDL No.MFCD00077166

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

3-(2-Thienyl)-D-alanine|CS-M2655

Structure of 62561-76-6

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General Information

  • CAS No. 62561-76-6
  • Cat. No. CS-M2655
  • Purity ≥98%
  • MDL No. MFCD00077166
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₉NO₂S
  • Molecular Weight 171.22
  • Synonym(s) D-3-(2-Thienyl)alanine
  • SMILES N[C@H](CC1=CC=CS1)C(O)=O

Description

3-(2-Thienyl)-D-alanine is a non-proteinogenic amino acid featuring a thiophene ring directly fused to the alpha carbon. This configuration imparts enhanced metabolic stability and unique electronic properties, enabling its use in peptidomimetic design and bioactive compound synthesis where aromaticity and conformational rigidity are critical.

Application

3-(2-Thienyl)-D-alanine serves as a valuable chiral building block for the synthesis of thienyl-containing peptidomimetics and bioactive heterocyclic compounds. Its D-amino acid configuration and electron-rich thiophene moiety enable compatibility with standard coupling protocols, offering enhanced metabolic stability and defined stereochemistry in medicinal chemistry applications. The compound exhibits bench-stable properties and facilitates efficient incorporation into peptide scaffolds via conventional amide bond formation.

Synthesis

  • Route1

    References

    • Paizs, Csaba; Katona, Adrian; Retey, Janos Chemistry - A European Journal, 2006 , vol. 12, # 10 p. 2739 - 2744
  • Route2

    References

    • Journal of Organic Chemistry, , vol. 74, # 18 p. 6953 - 6959
  • Route3

    References

    • Chemistry - A European Journal, , vol. 12, # 10 p. 2739 - 2744

Safety Information

Download SDS
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-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   63.32
  • LogP   0.7025
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   3

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