(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-((1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl)amino)pentanoic acid

Name: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-((1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl)amino)pentanoic acid
Brand: ChemScene
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CAS No. 269062-80-8
Cat. No. CS-0020129
Purity≥95%
MDL No.MFCD01862895

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(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-((1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl)amino)pentanoic acid|CS-0020129

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General Information

CAS No. 269062-80-8
Cat. No. CS-0020129
Purity ≥95%
MDL No. MFCD01862895
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃₀H₃₄N₂O₆
Molecular Weight 518.60
Synonym(s) Fmoc-Orn(Dde)-OH
SMILES O=C(O)[C@H](CCCN/C(C)=C1C(CC(C)(C)CC\1=O)=O)NC(OCC2C3=C(C4=C2C=CC=C4)C=CC=C3)=O

Description

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-((1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl)amino)pentanoic acid features a fluorenylmethoxycarbonyl (Fmoc) protecting group for robust N-terminal stabilization during peptide synthesis. The pendant cyclohexanedione-derived side chain introduces a sterically hindered, electron-deficient moiety that enhances solubility and facilitates selective coupling under mild conditions. This configuration supports efficient incorporation into complex peptide architectures with minimal epimerization.

Application

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-((1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl)amino)pentanoic acid serves as a versatile chiral building block for peptide synthesis and medicinal chemistry applications. Its fluorenylmethoxycarbonyl (Fmoc) group enables efficient N-terminal protection with orthogonal deprotection, while the cyclohexanedione-derived side chain provides a rigid, electron-deficient moiety suitable for bioisosteric replacement. The molecule exhibits bench stability, facilitates purification by standard chromatography, and participates reliably in amide coupling reactions under common conditions.

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 : 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

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Computational Chemistry Data

TPSA 121.8
LogP 4.5803
H_Acceptors 6
H_Donors 3
Rotatable_Bonds 9

Other Classifications

Building Blocks Functional Group Fmoc

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-((1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl)amino)pentanoic acid

CAS No. 269062-80-8

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