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CS-W001157 4
Total: USD 88.00

S-tert-Leucine N-methylamide

  • CAS No. 89226-12-0

  • Cat. No. CS-M2950
  • Molecule weight144.21
  • Purity≥95%
  • MDL No.MFCD00673329

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

S-tert-Leucine N-methylamide|CS-M2950

Structure of 89226-12-0

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General Information

  • CAS No. 89226-12-0
  • Cat. No. CS-M2950
  • Purity ≥95%
  • MDL No. MFCD00673329
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₆N₂O
  • Molecular Weight 144.21
  • Synonym(s) Butanamide, 2-amino-N,3,3-trimethyl-, (S)-; (S)-2-Amino-N-methyl-3,3-dimethylbutanamide; L-tert-Leucine methylamide; L-tert-Leucine-N-methylamide
  • SMILES N[C@@H](C(C)(C)C)C(NC)=O

Description

S-tert-Leucine N-methylamide features a sterically hindered side chain and a stable N-methylamide terminus, enabling enhanced metabolic resistance and improved membrane permeability. This configuration supports efficient incorporation into peptide sequences under standard conditions, offering robust stability in bioactive peptide synthesis workflows.

Application

S-tert-Leucine N-methylamide serves as a valuable chiral building block in peptide synthesis, offering enhanced metabolic stability and improved membrane permeability compared to its parent amino acid. The N-methylated amide functionality reduces hydrogen bonding capacity while maintaining backbone conformational rigidity, facilitating incorporation into bioactive peptides. Its tert-leucine side chain provides steric bulk that can modulate proteolytic resistance and target binding affinity, making it particularly useful in medicinal chemistry campaigns targeting peptidomimetics and macrocyclic scaffolds.

Synthesis

  • Route1
    • (S)-tert-butyl (3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)carbamate(WXC08256)|CS-0011409
      200865-04-9
    • ~79%
    • In-stock
      S-tert-Leucine N-methylamide|CS-M2950
      89226-12-0

    References

    • Glaxo Wellcome Inc. Patent: US6172064 B2, 2001 ; US 6172064 B1
  • Route2
    • null|null
      75-36-5
    • In-stock
      (S)-2-(Methoxycarbonylamino)-3,3-dimethylbutanoic acid|CS-B0635
      162537-11-3
    • ~95%
    • In-stock
      S-tert-Leucine N-methylamide|CS-M2950
      89226-12-0

    References

    • DSM N.V. Patent: US2001/41812 A1, 2001 ;
  • Route3
    • null|null
      75-36-5
    • null|null
      74-89-5
    • In-stock
      (S)-2-(Methoxycarbonylamino)-3,3-dimethylbutanoic acid|CS-B0635
      162537-11-3
    • ~%
    • In-stock
      S-tert-Leucine N-methylamide|CS-M2950
      89226-12-0

    References

    • US2001/41812 A1, ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362+P364

Quality Control

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Computational Chemistry Data

  • TPSA   55.12
  • LogP   0.1058
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   1

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