(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid

Name: (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid
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CAS No. 288617-76-5
Cat. No. CS-W005913
Molecule weight351.40
Purity≥96%
MDL No.MFCD08063323

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(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid|CS-W005913

Structure of 288617-76-5

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General Information

CAS No. 288617-76-5
Cat. No. CS-W005913
Purity ≥96%
MDL No. MFCD08063323
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₁H₂₁NO₄
Molecular Weight 351.40
Synonym(s) None
SMILES C=CC[C@@](NC(OCC1C2=C(C=CC=C2)C3=C1C=CC=C3)=O)(C(O)=O)C

Description

This chiral building block features a fluorenylmethoxycarbonyl-protected amino acid with a conjugated enoic acid side chain. The (R)-stereochemistry at the alpha carbon ensures high fidelity in peptide coupling, while the fluoren-9-ylmethoxycarbonyl group enables efficient orthogonal protection. The electron-rich enoate moiety facilitates downstream functionalization and participates in conjugate addition reactions under mild conditions.

Application

(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid serves as a valuable chiral building block in peptide synthesis, enabling efficient incorporation of sterically hindered, non-natural amino acid residues. The fluorenylmethoxycarbonyl (Fmoc) group provides excellent stability under basic conditions and facilitates rapid, quantitative removal during standard deprotection protocols. The α-methyl and pent-4-enoic functionalities offer enhanced metabolic stability and conformational rigidity, making this intermediate particularly useful for constructing bioactive peptide scaffolds with improved pharmacokinetic profiles.

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

Quality Control

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Computational Chemistry Data

TPSA 75.63
LogP 3.9445
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Bioactive Molecules Peptides

Building Blocks Functional Group Fmoc

Life Science Amino Acids and their Derivatives Alanine and derivatives

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid

CAS No. 288617-76-5

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