Fmoc-L-5-fluoroTryptophan

Name: Fmoc-L-5-fluoroTryptophan
Brand: ChemScene
Availability: InStock
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CAS No. 908846-88-8
Cat. No. CS-0012678
Molecule weight444.45
Purity≥98%
MDL No.MFCD24842544

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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 908846-88-8

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General Information

CAS No. 908846-88-8
Cat. No. CS-0012678
Purity ≥98%
MDL No. MFCD24842544
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₆H₂₁FN₂O₄
Molecular Weight 444.45
Synonym(s) N-Fmoc-5-fluoro-L-tryptophan
SMILES O=C(O)[C@H](CC1=CNC2=CC=C(F)C=C12)NC(OCC3C4=C(C5=C3C=CC=C5)C=CC=C4)=O

Description

Fmoc-L-5-fluoroTryptophan integrates a fluorinated indole ring into peptide synthesis, enabling site-specific bioorthogonal labeling and structural probing. This bench-stable derivative features enhanced electron-withdrawing character, facilitating controlled incorporation into polypeptide chains under standard coupling conditions.

Application

Fmoc-L-5-fluoroTryptophan serves as a valuable building block for solid-phase peptide synthesis, enabling site-specific incorporation of fluorinated tryptophan residues. The Fmoc group provides orthogonal protection compatible with standard coupling protocols, while the 5-fluoro substitution offers enhanced metabolic stability and modulates electronic properties without compromising backbone compatibility. This derivative exhibits excellent bench stability, facilitates straightforward purification, and functions effectively in diverse synthetic workflows involving bioactive peptide scaffolds.

Synthesis

Route1
- 102774-86-7
- In-stock
  
  16626-02-1
- ~94%
- In-stock
  
  908846-88-8
References
- Blaser, Georg; Sanderson, John M.; Batsanov, Andrei S.; Howard, Judith A.K. Tetrahedron Letters, 2008 , vol. 49, # 17 p. 2795 - 2798

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 91.42
LogP 4.8414
H_Acceptors 3
H_Donors 3
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Fluoride

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

Key Words

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Fmoc-L-5-fluoroTryptophan

CAS No. 908846-88-8

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