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N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(pent-4-ynoyl)-L-lysine

  • CAS No. 1159531-18-6

  • Cat. No. CS-0539115
  • Molecule weight448.51
  • Purity≥97%
  • MDL No.None

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

N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(pent-4-ynoyl)-L-lysine|CS-0539115

Structure of 1159531-18-6

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General Information

  • CAS No. 1159531-18-6
  • Cat. No. CS-0539115
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₆H₂₈N₂O₅
  • Molecular Weight 448.51
  • Synonym(s) Nα-Fmoc-Nβ-4-pentynoyl-L-lysine
  • SMILES C#CCCC(=O)NCCCC[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Description

This protected lysine derivative features a fluorenylmethoxycarbonyl group at the Nα position and a pent-4-ynoyl moiety at the Nε terminus, enabling orthogonal functionalization in peptide synthesis. The fluoren-9-yl methoxycarbonyl (Fmoc) handle ensures stable, acid-labile protection, while the terminal alkyne facilitates bioorthogonal coupling via copper-catalyzed azide-alkyne cycloaddition. This structure supports modular assembly of complex peptides and conjugates under standard conditions.

Application

N₂-(((9H-fluoren-9-yl)methoxy)carbonyl)-N⁶-(pent-4-ynoyl)-L-lysine serves as a versatile dipeptide building block for solid-phase peptide synthesis, combining the orthogonal Fmoc group for Nα protection with a terminal alkyne functionality. The pent-4-ynoyl side chain enables bioorthogonal conjugation via copper-catalyzed azide-alkyne cycloaddition (CuAAC), facilitating site-specific labeling or macrocyclization. Its bench-stable, crystalline nature and compatibility with standard coupling protocols make it ideal for modular peptide assembly and probe development in medicinal chemistry workflows.

Safety Information

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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   104.73
  • LogP   3.6782
  • H_Acceptors   4
  • H_Donors   3
  • Rotatable_Bonds   11

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