N-Fmoc-6-methyl-L-tryptophan

Name: N-Fmoc-6-methyl-L-tryptophan
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CAS No. 908846-99-1
Cat. No. CS-0439438
Molecule weight440.49
Purity≥98%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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General Information

CAS No. 908846-99-1
Cat. No. CS-0439438
Purity ≥98%
MDL No. None
Storage 4°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₇H₂₄N₂O₄
Molecular Weight 440.49
Synonym(s) N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-6-methyl-L-tryptophan
SMILES C(OC(N[C@@H](CC=1C=2C(NC1)=CC(C)=CC2)C(O)=O)=O)C3C=4C(C=5C3=CC=CC5)=CC=CC4

Description

N-Fmoc-6-methyl-L-tryptophan integrates a sterically hindered methyl group at the 6-position of the indole ring, enhancing metabolic stability while preserving bioactive conformation. This derivative enables direct incorporation into peptide chains under standard coupling conditions, offering improved resistance to enzymatic degradation in biological assays and synthetic applications.

Application

N-Fmoc-6-methyl-L-tryptophan serves as a valuable building block in peptide synthesis, enabling site-specific incorporation of a methylated tryptophan residue. The Fmoc group provides orthogonal protection for the amine, allowing selective deprotection during solid-phase synthesis. The 6-methyl substitution enhances metabolic stability and modulates electronic properties, making this derivative particularly useful in medicinal chemistry for optimizing peptide ligands and bioactive scaffolds.

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-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P501

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Computational Chemistry Data

TPSA 91.42
LogP 5.01072
H_Acceptors 3
H_Donors 3
Rotatable_Bonds 6

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Tryptophan and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Amino Acid Derivatives

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N-Fmoc-6-methyl-L-tryptophan

CAS No. 908846-99-1

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