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CS-W001157 4
Total: USD 88.00

L-Cyclohexylalanine

  • CAS No. 27527-05-5

  • Cat. No. CS-W002450
  • Purity≥97%
  • MDL No.MFCD00153484

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

L-Cyclohexylalanine|CS-W002450

Structure of 27527-05-5

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General Information

  • CAS No. 27527-05-5
  • Cat. No. CS-W002450
  • Purity ≥97%
  • MDL No. MFCD00153484
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₇NO₂
  • Molecular Weight 171.24
  • Synonym(s) None
  • SMILES OC([C@@H](N)CC1CCCCC1)=O

Description

L-Cyclohexylalanine features a cyclohexyl side chain that imparts enhanced hydrophobicity and steric bulk, enabling strategic incorporation into peptide sequences to modulate conformational stability, membrane permeability, and target binding affinity in bioactive molecule design.

Application

L-Cyclohexylalanine serves as a valuable non-proteinogenic amino acid building block in peptide synthesis, offering enhanced lipophilicity and conformational rigidity due to its cyclohexyl side chain. It facilitates improved membrane permeability and metabolic stability in bioactive peptides, while maintaining compatibility with standard coupling protocols and orthogonal protecting group strategies. Its bench-stable solid form enables straightforward handling and purification in iterative synthetic workflows.

Synthesis

  • Route1
    • L-Phenylalanine Aspartame Impurity|CS-0229723
      63-91-2
    • ~10%
    • In-stock
      L-Cyclohexylalanine|CS-W002450
      27527-05-5

    References

    • Hoekstra, William J.; Sunder, Shyam S.; Cregge, Robert J.; Ashton, Louis A.; Stewart, Kenneth T.; King, Chi-Hsin R. Tetrahedron, 1992 , vol. 48, # 2 p. 307 - 318
  • Route2

    References

    • Suarez, Rosa M.; Sestelo, Jose Perez; Sarandeses, Luis A. Organic and Biomolecular Chemistry, 2004 , vol. 2, # 24 p. 3584 - 3587
  • Route3
    • null|null
      163085-09-4
    • ~%
    • In-stock
      L-Cyclohexylalanine|CS-W002450
      27527-05-5

    References

    • Suarez, Rosa M.; Sestelo, Jose Perez; Sarandeses, Luis A. Organic and Biomolecular Chemistry, 2004 , vol. 2, # 24 p. 3584 - 3587

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

Quality Control

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Computational Chemistry Data

  • TPSA   63.32
  • LogP   1.3687
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   3

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