Methyl acetyl-L-tryptophanate

Name: Methyl acetyl-L-tryptophanate
Brand: ChemScene
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CAS No. 2824-57-9
Cat. No. CS-0112520
Purity≥97%
MDL No.MFCD00022759

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FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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Methyl acetyl-L-tryptophanate|CS-0112520

Structure of 2824-57-9

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General Information

CAS No. 2824-57-9
Cat. No. CS-0112520
Purity ≥97%
MDL No. MFCD00022759
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₆N₂O₃
Molecular Weight 260.29
Synonym(s) Methyl N-acetyl-L-tryptophanate
SMILES O=C(OC)[C@@H](NC(C)=O)CC1=CNC2=C1C=CC=C2

Description

Methyl acetyl-L-tryptophanate features a protected indole side chain and acetylated amine, enabling stable incorporation into peptide synthesis workflows. This derivative delivers enhanced solubility and resistance to hydrolysis under standard conditions, simplifying purification and handling in complex coupling reactions.

Application

Methyl acetyl-L-tryptophanate serves as a protected L-tryptophan derivative, enabling controlled incorporation into peptide synthesis. The acetyl group at the amine and methyl ester at the carboxyl terminus provide enhanced stability and simplified purification. It functions effectively in standard coupling protocols, offering reliable reactivity with minimal epimerization, making it a practical building block for complex peptide architectures and heterocyclic scaffold development.

Synthesis

Route1
- In-stock
  
  7524-52-9
- 507-09-5
- ~99%
- In-stock
  
  2824-57-9
References
- Crich, David; Sharma, Indrajeet Angewandte Chemie, International Edition, 2009 , vol. 48, # 13 p. 2355 - 2358
Route2
- 123972-87-2
- In-stock
  
  1218-34-4
- ~84%
- In-stock
  
  2824-57-9
References
- Boivin, Jean; Henriet, Eric; Zard, Samir Z. Journal of the American Chemical Society, 1994 , vol. 116, # 21 p. 9739 - 9740
Route3
- 108-24-7
- In-stock
  
  7524-52-9
- ~97%
- In-stock
  
  2824-57-9
References
- Ruiz-Rodriguez, Javier; Albericio, Fernando; Lavilla, Rodolfo Chemistry - A European Journal, 2010 , vol. 16, # 4 p. 1124 - 1127

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-H315-H319-H335
Precautionary Statements : P233-P260-P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 71.19
LogP 1.3881
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

Chemical Biology Peptide Chemistry Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Peptide Chemistry Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Peptide Chemistry Amino Acid Derivatives

Biochemistry Biochemicals and Reagents Amino Acids C-ProtectedAmino Acids

Biochemistry Biochemicals and Reagents Amino Acids N-Protected Amino Acids

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Methyl acetyl-L-tryptophanate

CAS No. 2824-57-9

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