L-7-Azatryptophan

Name: L-7-Azatryptophan
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 49758-35-2
Cat. No. CS-0004126
Purity≥97%
MDL No.MFCD08272984

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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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Structure of 49758-35-2

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General Information

CAS No. 49758-35-2
Cat. No. CS-0004126
Purity ≥97%
MDL No. MFCD08272984
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₁N₃O₂
Molecular Weight 205.21
Synonym(s) 7-Aza-L-tryptophan
SMILES O=C(O)[C@@H](N)CC1=CNC2=NC=CC=C21

Description

L-7-Azatryptophan features a nitrogen substitution at the C7 position of the indole ring, introducing a polar, electron-deficient moiety that enhances solubility and alters binding interactions. This analog integrates seamlessly into peptide sequences under standard coupling conditions, enabling site-specific incorporation to probe protein structure-function relationships and modulate pharmacokinetic properties in bioactive peptides.

Application

L-7-Azatryptophan serves as a bioisostere of tryptophan, enabling targeted incorporation into peptides to probe indole ring functionality in biological systems. Its pyrrole nitrogen substitution enhances metabolic stability and modulates electronic properties, facilitating studies in receptor binding and protein folding. The compound exhibits robust bench stability and compatibility with standard solid-phase peptide synthesis protocols, offering reliable access to labeled or modified biologically active sequences.

Synthesis

Route1
- 63024-18-0
- ~45%
- In-stock
  
  49758-35-2
References
- Lecointe; Rolland-Fulcrand; Roumestant; Viallefont; Martinez Tetrahedron Asymmetry, 1998 , vol. 9, # 10 p. 1753 - 1758
Route2
- 211179-97-4
- ~%
- In-stock
  
  49758-35-2
References
- Lecointe; Rolland-Fulcrand; Roumestant; Viallefont; Martinez Tetrahedron Asymmetry, 1998 , vol. 9, # 10 p. 1753 - 1758

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 : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 92
LogP 0.5173
H_Acceptors 3
H_Donors 3
Rotatable_Bonds 3

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Chemical Biology Peptide Chemistry Amino Acid Derivatives

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L-7-Azatryptophan

CAS No. 49758-35-2

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