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(R)-2-Aminopent-4-ynoic acid hydrochloride

  • CAS No. 87205-47-8

  • Cat. No. CS-0158576
  • Purity≥97%
  • MDL No.MFCD09263338

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

(R)-2-Aminopent-4-ynoic acid hydrochloride|CS-0158576

Structure of 87205-47-8

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General Information

  • CAS No. 87205-47-8
  • Cat. No. CS-0158576
  • Purity ≥97%
  • MDL No. MFCD09263338
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₈ClNO₂
  • Molecular Weight 149.58
  • Synonym(s) R-2-Amino-4-Pentynoic acid
  • SMILES C#CC[C@@H](N)C(O)=O.Cl

Description

(R)-2-Aminopent-4-ynoic acid hydrochloride features a chiral α-amino acid scaffold with a terminal alkyne handle, enabling bioorthogonal conjugation in peptide and probe synthesis. The hydrochloride salt enhances solubility and stability under standard bench conditions, facilitating straightforward handling in aqueous and organic media. This derivative integrates efficiently into diverse molecular architectures through click chemistry or amide coupling protocols.

Application

(R)-2-Aminopent-4-ynoic acid hydrochloride serves as a versatile building block for the synthesis of bioactive heterocycles and peptidomimetics. Its terminal alkyne and α-amino carboxylic acid functionalities enable efficient copper-catalyzed azide-alkyne cycloaddition (CuAAC) and direct incorporation into peptide chains. The hydrochloride salt enhances bench stability and simplifies handling, while the stereochemically defined (R)-configuration ensures predictable reactivity in asymmetric synthesis.

Synthesis

  • Route1
    • null|null
      23235-02-1
    • ~99%
    • In-stock
      (R)-2-Aminopent-4-ynoic acid hydrochloride|CS-0158576
      87205-47-8

    References

    • Baldwin, Jack E.; Bradley, Mark; Abbott, Shaun D.; Adlington, Robert M. Tetrahedron, 1991 , vol. 47, # 28 p. 5309 - 5328
  • Route2
    • Diethyl Acetamido(2-propyn-1-yl)malonate|CS-0759968
      61172-60-9
    • ~%
    • In-stock
      (R)-2-Aminopent-4-ynoic acid hydrochloride|CS-0158576
      87205-47-8

    References

    • Tetrahedron, , vol. 47, # 28 p. 5309 - 5328

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   -0.1566
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   2

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