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N-Fmoc-N'-methyl-L-asparagine

  • CAS No. 149204-93-3

  • Cat. No. CS-0160385
  • Purity≥97%
  • MDL No.MFCD30533782

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

N-Fmoc-N'-methyl-L-asparagine|CS-0160385

Structure of 149204-93-3

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General Information

  • CAS No. 149204-93-3
  • Cat. No. CS-0160385
  • Purity ≥97%
  • MDL No. MFCD30533782
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₀H₂₀N₂O₅
  • Molecular Weight 368.38
  • Synonym(s) N2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-asparagine
  • SMILES O=C(NC)C[C@@H](C(O)=O)NC(OCC1C2=CC=CC=C2C3=CC=CC=C13)=O

Description

N-Fmoc-N'-methyl-L-asparagine features a protected α-amino group and a methylated side chain, enabling selective coupling in peptide synthesis. The Fmoc moiety ensures orthogonal deprotection, while the N'-methyl substitution reduces backbone hydrogen bonding, enhancing solubility and minimizing aggregation during elongation. This derivative streamlines access to complex peptidomimetics.

Application

N-Fmoc-N'-methyl-L-asparagine serves as a key building block in peptide synthesis, enabling efficient incorporation of side-chain functionalized asparagine residues. The Fmoc group provides orthogonal protection for the α-amino function, allowing selective deprotection under mild basic conditions. The N'-methyl substitution enhances conformational rigidity and metabolic stability, while the β-carboxamide side chain supports hydrogen bonding in structural motifs. This derivative exhibits excellent bench stability, compatibility with standard coupling reagents, and facilitates purification via standard chromatographic methods.

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-P302+P352-P304+P340

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Computational Chemistry Data

  • TPSA   104.73
  • LogP   2.1144
  • H_Acceptors   4
  • H_Donors   3
  • Rotatable_Bonds   6

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