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

CAS No. 1290040-14-0
Cat. No. CS-0527294
Purity≥98%
MDL No.None

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

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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.

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

Computational Chemistry Data

TPSA 104.73
LogP 4.1043
H_Acceptors 4
H_Donors 3
Rotatable_Bonds 6

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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Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Indolin compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Glutamine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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

CAS No. 1290040-14-0

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