(3R)-4-Amino-3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-oxobutanoic acid

Name: (3R)-4-Amino-3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-oxobutanoic acid
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CAS No. 200335-41-7
Cat. No. CS-0208777
Molecule weight354.36
Purity≥95%
MDL No.MFCD00237392

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(3R)-4-Amino-3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-oxobutanoic acid|CS-0208777

Structure of 200335-41-7

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General Information

CAS No. 200335-41-7
Cat. No. CS-0208777
Purity ≥95%
MDL No. MFCD00237392
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₉H₁₈N₂O₅
Molecular Weight 354.36
Synonym(s) Fmoc-D-asp-NH2
SMILES O=C(O)C[C@H](C(N)=O)NC(OCC1C2=CC=CC=C2C3=CC=CC=C31)=O

Description

This fluorenylmethoxycarbonyl-protected amino acid derivative features a chiral (3R) configuration and a reactive ketone moiety, enabling site-specific conjugation in peptide synthesis. The C-terminal carbonyl group facilitates efficient coupling reactions under standard conditions, while the fluorenylmethoxycarbonyl group provides robust protection and orthogonal deprotection compatibility. This structure supports the incorporation of biologically active motifs into complex peptides with high fidelity.

Application

(3R)-4-Amino-3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-oxobutanoic acid serves as a key chiral building block for the synthesis of peptidomimetics and β-amino acid derivatives. The Fmoc group provides orthogonal protection for the amine, enabling selective deprotection during solid-phase peptide synthesis. Its α,β-unsaturated carbonyl system facilitates conjugate addition reactions and participates in standard coupling protocols with high functional group tolerance. Bench-stable and readily purified by flash chromatography, it functions effectively in multi-step synthetic sequences requiring precise stereocontrol.

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 118.72
LogP 1.8537
H_Acceptors 4
H_Donors 3
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Carboxylic Acid

Building Blocks Functional Group Amide

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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(3R)-4-Amino-3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-oxobutanoic acid

CAS No. 200335-41-7

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