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Fmoc-(S)-2,3-dihydro-2-Oxo-Tryptophan

  • CAS No. 1290040-14-0

  • Cat. No. CS-0527294
  • Purity≥98%
  • MDL No.None

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

Fmoc-(S)-2,3-dihydro-2-Oxo-Tryptophan|CS-0527294

Structure of 1290040-14-0

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General Information

  • CAS No. 1290040-14-0
  • Cat. No. CS-0527294
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₆H₂₂N₂O₅
  • Molecular Weight 442.46
  • Synonym(s) Fmoc-S-2,3-dihydro-2-oxo-Tryptophan
  • SMILES O=C1NC2=CC=CC=C2C1C[C@@H](C(O)=O)NC(OCC3C4=CC=CC=C4C5=CC=CC=C53)=O

Description

Fmoc-(S)-2,3-dihydro-2-oxo-tryptophan is a specialized amino acid derivative featuring a protected indole ring and a keto functionality at the 2-position. This configuration enhances stability during peptide synthesis while enabling selective derivatization at the C2 site. The Fmoc group ensures efficient orthogonal deprotection, facilitating incorporation into complex sequences with minimal side reactions.

Application

Fmoc-(S)-2,3-dihydro-2-oxo-tryptophan serves as a stable, bench-friendly building block for the synthesis of constrained peptidomimetics and heterocyclic scaffolds. Its Fmoc-protected amine enables straightforward incorporation into solid-phase peptide synthesis, while the 2,3-dihydro-2-oxo functionality provides a versatile handle for selective transformations, including reductive amination and ring expansion. The compound exhibits excellent functional group tolerance and facilitates efficient purification, making it well-suited for medicinal chemistry campaigns requiring rigidified tryptophan analogs.

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 : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362+P364

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Computational Chemistry Data

  • TPSA   104.73
  • LogP   4.1043
  • H_Acceptors   4
  • H_Donors   3
  • Rotatable_Bonds   6

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