N-Fmoc-N'-methyl-L-asparagine

Name: N-Fmoc-N'-methyl-L-asparagine
Brand: ChemScene
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CAS No. 149204-93-3
Cat. No. CS-0160385
Purity≥97%
MDL No.MFCD30533782

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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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N-Fmoc-N'-methyl-L-asparagine|CS-0160385

Structure of 149204-93-3

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Description

N-Fmoc-N'-methyl-L-asparagine features a protected α-amino group and a methylated side chain, enabling selective coupling in peptide synthesis. The Fmoc moiety ensures orthogonal deprotection, while the N'-methyl substitution reduces backbone hydrogen bonding, enhancing solubility and minimizing aggregation during elongation. This derivative streamlines access to complex peptidomimetics.

Application

N-Fmoc-N'-methyl-L-asparagine serves as a key building block in peptide synthesis, enabling efficient incorporation of side-chain functionalized asparagine residues. The Fmoc group provides orthogonal protection for the α-amino function, allowing selective deprotection under mild basic conditions. The N'-methyl substitution enhances conformational rigidity and metabolic stability, while the β-carboxamide side chain supports hydrogen bonding in structural motifs. This derivative exhibits excellent bench stability, compatibility with standard coupling reagents, and facilitates purification via standard chromatographic methods.

General Information

CAS No. 149204-93-3
Cat. No. CS-0160385
Purity ≥97%
MDL No. MFCD30533782
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₂₀N₂O₅
Molecular Weight 368.38
Synonym(s) N2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-asparagine
SMILES O=C(NC)C[C@@H](C(O)=O)NC(OCC1C2=CC=CC=C2C3=CC=CC=C13)=O

Computational Chemistry Data

TPSA 104.73
LogP 2.1144
H_Acceptors 4
H_Donors 3
Rotatable_Bonds 6

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-P302+P352-P304+P340

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Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Asparagine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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N-Fmoc-N'-methyl-L-asparagine

CAS No. 149204-93-3

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