Fmoc-N-Me-D-Trp(Boc)-OH

Name: Fmoc-N-Me-D-Trp(Boc)-OH
Brand: ChemScene
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CAS No. 2044709-90-0
Cat. No. CS-0166897
Purity≥97%
MDL No.MFCD30475981

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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. 2044709-90-0
Cat. No. CS-0166897
Purity ≥97%
MDL No. MFCD30475981
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃₂H₃₂N₂O₆
Molecular Weight 540.61
Synonym(s) None
SMILES CC(C)(C)OC(N1C2=CC=CC=C2C(C[C@H](C(O)=O)N(C)C(OCC3C4=CC=CC=C4C5=CC=CC=C53)=O)=C1)=O

Description

Fmoc-N-Me-D-Trp(Boc)-OH is a stereochemically defined, bench-stable building block for peptide synthesis featuring a protected indole side chain. The N-methylated D-tryptophan moiety enhances conformational rigidity and metabolic stability, while the Fmoc group enables efficient C-terminal coupling under standard conditions. This derivative supports the incorporation of D-Trp residues with enhanced resistance to enzymatic degradation in bioactive peptide sequences.

Application

Fmoc-N-Me-D-Trp(Boc)-OH serves as a key building block for the synthesis of D-amino acid-containing peptides, particularly in solid-phase peptide synthesis. The Fmoc group enables efficient orthogonal deprotection under mild basic conditions, while the N-methyl and Boc-protected indole side chain provide enhanced metabolic stability and reduced backbone hydrogen bonding. Its bench-stable nature and compatibility with standard coupling protocols facilitate reliable incorporation into complex peptide sequences.

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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Precautionary Statements : N/A

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Computational Chemistry Data

TPSA 98.07
LogP 6.3011
H_Acceptors 6
H_Donors 1
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Boc

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-N-Me-D-Trp(Boc)-OH

CAS No. 2044709-90-0

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