cis-2-(Fmoc-amino)-cyclohexanecarboxylic acid, CAS No. 194471-85-7

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194471-85-7

Catalog No. EBD3316463

CAS 194471-85-7

Name cis-2-(Fmoc-amino)-cyclohexanecarboxylic acid

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Basic Information

Synonyms: (1r,2s/1s,2r)-cis-1-(9-fluorenylmethyloxycarbonyl-amino)-cyclohexyl-2-carboxylicacid fmoc-1,2-cis-achc-oh fmoc-cis-2-amino-1-cyclohexanecarboxylicacid fmoc-(+/-)-cis-2-aminocyclohexane-1-carboxylicacid fmoc-cis-2-aminocyclohexanecarboxylicacid fmoc-cis-1,2-aminocyclohexanecarboxylicacid fmoc-cis-beta-amino-alpha-cyclohexanecarboxylicacid cis-1-(9-fluorenylmethyloxycarbonylamino)-cyclohexyl-2-carboxylicacid cis-2-(Fmoc-amino)-cyclohexanecarboxylicacid (1R,2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}cyclohexanecarboxylicacid

Molecular Formula: C22H23NO4

Molecular Weight: 365.42

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks Synthetic Chemistry > Organic Building Blocks > Amines

Product Description:

Cis-2-(Fmoc-amino)-cyclohexanecarboxylic acid is a protected amino acid derivative featuring a cyclohexane backbone. Its structure incorporates both an Fmoc (9-fluorenylmethoxycarbonyl) protected amino group and a free carboxylic acid group in a cis-configuration relative to the cyclohexane ring. This bifunctional nature makes it a versatile chiral building block. This compound is primarily employed in solid-phase peptide synthesis (SPPS) and the synthesis of peptidomimetics. The Fmoc group serves as a base-labile protecting group for the amine, allowing for orthogonal deprotection strategies during sequential peptide chain assembly. The cis-cyclohexane scaffold is valued for introducing conformational constraints into peptide sequences, which can enhance metabolic stability, receptor selectivity, and bioavailability in drug discovery programs targeting various diseases. As a specialized, non-proteinogenic amino acid derivative, it is a key intermediate in medicinal chemistry research for developing novel therapeutic agents. Its applications are firmly rooted in pharmaceutical development rather than as a general-purpose chemical reagent.

Physical Properties

Boiling Point: 596.9 °C at 760 mmHg

Flash Point: 314.8 °C

Density: 1.29 g/cm3

Storage: 2-8°C