(1S,2S)-Fmoc-2-aminocyclohexane carboxylic acid

Name: (1S,2S)-Fmoc-2-aminocyclohexane carboxylic acid
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CAS No. 312965-07-4
Cat. No. CS-0207684
Molecule weight365.42
Purity≥98%
MDL No.MFCD05663771

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(1S,2S)-Fmoc-2-aminocyclohexane carboxylic acid|CS-0207684

Structure of 312965-07-4

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General Information

CAS No. 312965-07-4
Cat. No. CS-0207684
Purity ≥98%
MDL No. MFCD05663771
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₂H₂₃NO₄
Molecular Weight 365.42
Synonym(s) (1S,2S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclohexanecarboxylic acid
SMILES O=C([C@@H]1[C@@H](NC(OCC2C3=CC=CC=C3C4=CC=CC=C24)=O)CCCC1)O

Description

This chiral Fmoc-protected amino acid features a rigid cyclohexane scaffold, enabling precise conformational control in peptide synthesis. The (1S,2S) stereochemistry ensures high diastereoselectivity during coupling, while the Fmoc group facilitates efficient orthogonal deprotection. Ideal for incorporating constrained motifs into bioactive peptides and peptidomimetics.

Application

(1S,2S)-Fmoc-2-aminocyclohexane carboxylic acid serves as a chiral building block for the synthesis of bioactive peptides and cyclic scaffolds. The Fmoc group enables efficient solid-phase peptide synthesis, while the rigid cyclohexane core provides defined stereochemistry and conformational restraint. Its amine functionality facilitates diverse coupling reactions, and the carboxylic acid supports standard activation protocols. Bench-stable and readily purified by chromatography, it functions reliably in iterative synthesis workflows.

Synthesis

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  312965-07-4
References
- European Journal of Organic Chemistry, , # 4 p. 721 - 726
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References
- European Journal of Organic Chemistry, , # 4 p. 721 - 726
Route3
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  312965-07-4
References
- European Journal of Organic Chemistry, , # 4 p. 721 - 726

Safety Information

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Computational Chemistry Data

TPSA 75.63
LogP 4.1685
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Fatty ring compounds Cyclohexane compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

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(1S,2S)-Fmoc-2-aminocyclohexane carboxylic acid

CAS No. 312965-07-4

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