Fmoc-D-Pipecolic acid, CAS No. 101555-63-9

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101555-63-9

Catalog No. EBD27668

CAS 101555-63-9

Name Fmoc-D-Pipecolic acid

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Basic Information

Synonyms: Fmoc-D-Homopro-OH Fmoc-D-Pip-OH (2R)-1-[(9H-Fluoren-9-ylmethoxy)carbonyl]hexahydropyridine-2-carboxylicacid (2R)-1-[(9H-fluoren-9-ylmethoxy)carbonyl]piperidine-2-carboxylicacid 1-[(9H-fluoren-9-ylmethoxy)carbonyl]piperidine-2-carboxylicacid (2S)-1-[(9H-fluoren-9-ylmethoxy)carbonyl]piperidine-2-carboxylicacid N-alpha-(9-fluorenylmethoxycarbonyl)-D-homoproline N-alpha-(9-fluorenylmethoxycarbonyl)-D-Pipecolicacid N-alpha-Fmoc-D-Pipecolicacid N-Fmoc-(R)-pipecolinicacid N-Fmoc-D-pipecolinicacid RARECHEMARPA0006 (R)-N-(9-fluorenylmethyloxycarbonyl)-piperidine-2-carboxylicacid (R)-N-Fmoc-piperidine-2-carboxylicacid 2-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylicacid (2S)-1-[(9H-fluoren-9-ylme 1-Fmoc-piperidine-2-carboxylicacid Fmoc-D-HoPro-OH

Molecular Formula: C21H21NO4

Molecular Weight: 351.4

MDL Number: MFCD00235899

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates Medicinal Chemistry > Biochemicals and Life Science Reagents > Peptides and Peptidomimetics

Product Description:

Fmoc-D-Pipecolic acid is a protected, non-proteinogenic amino acid derivative. Its structure features a piperidine-2-carboxylic acid (pipecolic acid) core with a D-configuration at the alpha-carbon, which is protected by a 9-fluorenylmethoxycarbonyl (Fmoc) group on the nitrogen. This compound is a white to off-white crystalline powder. This building block is primarily used in solid-phase peptide synthesis (SPPS) as an Fmoc-protected amino acid. The D-enantiomer of pipecolic acid is incorporated into peptides to introduce conformational constraints, enhance metabolic stability, and modulate biological activity. It serves as a key intermediate in the research and development of peptide-based pharmaceuticals, including potential drug candidates for oncology, neurology, and infectious diseases. The Fmoc protecting group is selectively removable under mild basic conditions (e.g., piperidine), making it compatible with standard Fmoc-SPPS protocols. Its use is critical for constructing peptides containing this non-standard cyclic amino acid, which can mimic turn structures and improve the peptide's pharmacokinetic properties.

Physical Properties

Melting Point: 149-153°C

Boiling Point: 561.6 °C at 760 mmHg

Flash Point: 293.5 °C

Density: 1.293 g/cm3

Storage: 2-8°C

Analytical Data

Appearance: white to light yellow crystal powder