Fmoc-β-HomoTrp(Boc)-OH

Name: Fmoc-β-HomoTrp(Boc)-OH
Brand: ChemScene
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CAS No. 357271-55-7
Cat. No. CS-0188311
Purity≥95%
MDL No.MFCD09842083

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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. 357271-55-7
Cat. No. CS-0188311
Purity ≥95%
MDL No. MFCD09842083
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃₂H₃₂N₂O₆
Molecular Weight 540.61
Synonym(s) FMoc-β-HoMoTrp(Boc)-OH,FMoc-beta-HoMoTrp(Boc)-OH
SMILES C(OC(N[C@@H](CC=1C=2C(N(C(OC(C)(C)C)=O)C1)=CC=CC2)CC(O)=O)=O)C3C=4C(C=5C3=CC=CC5)=CC=CC4

Description

Fmoc-β-HomoTrp(Boc)-OH is a protected tryptophan derivative featuring a β-homologated side chain and orthogonal Boc protection. This variant enables precise incorporation into peptide sequences under standard coupling conditions, offering enhanced solubility and reduced aggregation during solid-phase synthesis. The Fmoc group facilitates efficient deprotection, while the Boc moiety remains stable through multiple reaction cycles.

Application

Fmoc-β-HomoTrp(Boc)-OH serves as a key building block for the synthesis of peptide-based scaffolds incorporating β-homotryptophan residues. The Fmoc group enables efficient N-terminal protection in solid-phase peptide synthesis, while the Boc-protected indole side chain offers orthogonal stability and compatibility with standard deprotection protocols. This derivative facilitates reliable incorporation of β-homotryptophan into complex peptides, supporting applications in medicinal chemistry and protein engineering.

Synthesis

Route1
- 357271-53-5
- ~69%
- In-stock
  
  357271-55-7
References
- Gademann; Kimmerlin; Hoyer; Seebach Journal of Medicinal Chemistry, 2001 , vol. 44, # 15 p. 2460 - 2468
Route2
- In-stock
  
  143824-78-6
- ~%
- In-stock
  
  357271-55-7
References
- Gademann; Kimmerlin; Hoyer; Seebach Journal of Medicinal Chemistry, 2001 , vol. 44, # 15 p. 2460 - 2468

Safety Information

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GHS Pictogram : N/A	GHS No : N/A
Signal Word : N/A	UN#: N/A
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Hazard Statements : N/A
Precautionary Statements : N/A

Quality Control

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Computational Chemistry Data

TPSA 106.86
LogP 6.349
H_Acceptors 6
H_Donors 2
Rotatable_Bonds 7

Other Classifications

Building Blocks Functional Group Boc

Building Blocks Functional Group Fmoc

Building Blocks Functional Group Amine

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Amino Acid Derivatives

Key Words

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Fmoc-β-HomoTrp(Boc)-OH

CAS No. 357271-55-7

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