Fmoc-α-Me-D-Trp(Boc)-OH

Name: Fmoc-α-Me-D-Trp(Boc)-OH
Brand: ChemScene
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CAS No. 220155-72-6
Cat. No. CS-0798470
Molecule weight540.61
Purity≥98%
MDL No.MFCD14636469

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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. 220155-72-6
Cat. No. CS-0798470
Purity ≥98%
MDL No. MFCD14636469
Storage 4°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃₂H₃₂N₂O₆
Molecular Weight 540.61
Synonym(s) None
SMILES O=C(O)[C@](CC1=CN(C(OC(C)(C)C)=O)C2=C1C=CC=C2)(C)NC(OCC3C4=C(C5=C3C=CC=C5)C=CC=C4)=O

Description

Fmoc-α-Me-D-Trp(Boc)-OH is a D-configured, α-methylated tryptophan derivative featuring a fluorenylmethyloxycarbonyl (Fmoc) protecting group and a tert-butoxycarbonyl (Boc) group on the indole nitrogen. This configuration enhances metabolic stability and resistance to enzymatic degradation during peptide synthesis. The electron-rich indole moiety facilitates efficient incorporation into complex peptide sequences, particularly in bioactive peptidomimetics and cyclic structures where conformational rigidity is advantageous.

Application

Fmoc-α-Me-D-Trp(Boc)-OH serves as a key building block for the synthesis of peptide libraries and bioactive oligomers, leveraging the D-configured tryptophan side chain for enhanced metabolic stability. The Fmoc group enables efficient solution-phase and solid-phase peptide coupling, while the Boc-protected indole nitrogen ensures orthogonal handling during sequential synthesis. This derivative exhibits excellent bench stability, facilitates straightforward purification, and supports diverse functionalization strategies in medicinal chemistry workflows.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H260-H301-H311-H314
Precautionary Statements : P223-P231+P232-P260-P264-P270-P280-P301+P330+P331-P302+P335+P334-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P330-P361+P364-P363-P370+P378-P402+P404-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 106.86
LogP 6.349
H_Acceptors 6
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Fmoc

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 Unnatural Amino Acid Derivatives

Key Words

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Fmoc-α-Me-D-Trp(Boc)-OH

CAS No. 220155-72-6

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