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2-Amino-2-methylbutanoic acid

  • CAS No. 595-39-1

  • Cat. No. CS-0311817
  • Purity≥98%
  • MDL No.MFCD00272968

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

2-Amino-2-methylbutanoic acid|CS-0311817

Structure of 595-39-1

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General Information

  • CAS No. 595-39-1
  • Cat. No. CS-0311817
  • Purity ≥98%
  • MDL No. MFCD00272968
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₁₁NO₂
  • Molecular Weight 117.15
  • Synonym(s) Isovaline
  • SMILES NC(C(O)=O)(CC)C

Description

2-Amino-2-methylbutanoic acid is a sterically hindered α-amino acid featuring a branched alkyl side chain. This structural motif enhances metabolic stability and influences conformational preferences in peptide design. The molecule integrates readily into synthetic peptides, serving as a key residue for probing steric effects in enzyme-substrate interactions.

Application

2-Amino-2-methylbutanoic acid serves as a valuable chiral building block in peptide synthesis and medicinal chemistry, offering a sterically hindered α-amino acid scaffold with enhanced metabolic stability. Its side chain supports diverse functionalization and participates reliably in standard coupling reactions, facilitating the construction of bioactive peptidomimetics and heterocyclic frameworks. The compound exhibits good bench stability and is compatible with common protecting group strategies.

Synthesis

  • Route1

    References

    • Chemical and pharmaceutical bulletin, , vol. 13, # 12 p. 1399 - 1407
  • Route2
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      151-50-8
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      78-93-3
    • ~%
    • In-stock
      2-Amino-2-methylbutanoic acid|CS-0311817
      595-39-1

    References

    • Journal of Biological Chemistry, , vol. 76, p. 313 Biochemische Zeitschrift, , vol. 134, p. 427
  • Route3
    • 2-Amino-2-methylbutanamide|CS-1661106
      59209-90-4
    • ~%
    • In-stock
      2-Amino-2-methylbutanoic acid|CS-0311817
      595-39-1

    References

    • Journal of Organic Chemistry USSR (English Translation), , vol. 20, p. 1243 - 1247 Zhurnal Organicheskoi Khimii, , vol. 20, # 7 p. 1367 - 1371

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   63.32
  • LogP   0.1984
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   2

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