(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5,5-dimethylhexanoic acid

Name: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5,5-dimethylhexanoic acid
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CAS No. 1217704-60-3
Cat. No. CS-0104683
Purity≥98%
MDL No.MFCD30533759

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(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5,5-dimethylhexanoic acid|CS-0104683

Structure of 1217704-60-3

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General Information

CAS No. 1217704-60-3
Cat. No. CS-0104683
Purity ≥98%
MDL No. MFCD30533759
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₃H₂₇NO₄
Molecular Weight 381.46
Synonym(s) N-Fmoc-5,5-dimethyl-L-norleucine
SMILES CC(C)(C)CC[C@@H](C(O)=O)NC(OCC1C2=CC=CC=C2C3=CC=CC=C13)=O

Description

This fluorenonyl-protected amino acid derivative features a sterically hindered, bench-stable side chain ideal for peptide synthesis. The (S)-configuration ensures stereochemical fidelity during coupling, while the Cbz group enables selective deprotection under mild hydrogenolysis conditions.

Application

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5,5-dimethylhexanoic acid serves as a robust chiral building block for peptide synthesis, offering excellent stability and ease of purification. The Fmoc group enables efficient N-terminal protection with orthogonal deprotection under mild basic conditions. The sterically hindered 5,5-dimethylhexanoyl side chain enhances conformational rigidity and metabolic stability, making it particularly valuable in the synthesis of bioactive peptides and peptidomimetics requiring enhanced proteolytic resistance.

Safety Information

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Computational Chemistry Data

TPSA 75.63
LogP 4.8046
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 6

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)-5,5-dimethylhexanoic acid

CAS No. 1217704-60-3

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