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(R)-5-Amino-2-((tert-butoxycarbonyl)amino)pentanoic acid

  • CAS No. 159877-12-0

  • Cat. No. CS-W007115
  • Molecule weight232.28
  • Purity≥95%
  • MDL No.MFCD00236869

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

(R)-5-Amino-2-((tert-butoxycarbonyl)amino)pentanoic acid|CS-W007115

Structure of 159877-12-0

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General Information

  • CAS No. 159877-12-0
  • Cat. No. CS-W007115
  • Purity ≥95%
  • MDL No. MFCD00236869
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₂₀N₂O₄
  • Molecular Weight 232.28
  • Synonym(s) N-ALPHA-TERT-BUTYLOXYCARBONYL-D-ORNITHINE
  • SMILES NCCC[C@H](C(O)=O)NC(OC(C)(C)C)=O

Description

(R)-5-Amino-2-((tert-butoxycarbonyl)amino)pentanoic acid is a stereochemically defined amino acid derivative featuring a protected primary amine and a carboxylic acid handle. This scaffold enables direct incorporation into peptide sequences or conjugation workflows under standard conditions, offering enhanced solubility and stability during synthesis and purification.

Application

(R)-5-Amino-2-((tert-butoxycarbonyl)amino)pentanoic acid serves as a key chiral building block for the synthesis of bioactive peptides and heterocyclic scaffolds. The Boc-protected amine and carboxylic acid functionalities enable orthogonal derivatization, while the (R)-configuration ensures stereochemical fidelity in downstream transformations. This compound exhibits excellent bench stability, facilitates straightforward purification via standard chromatography, and functions reliably in coupling reactions and cyclization protocols common to medicinal chemistry workflows.

Synthesis

  • Route1

    References

    • Semple; Rowley; Brunck; Ha-Uong; Minami; Owens; Tamura; Goldman; Siev; Ardecky; Carpenter; Ge; Richard; Nolan; Hakanson; Tulinsky; Nutt; Ripka Journal of Medicinal Chemistry, 1996 , vol. 39, # 23 p. 4531 - 4536

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   101.65
  • LogP   0.7032
  • H_Acceptors   4
  • H_Donors   3
  • Rotatable_Bonds   5

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