105751-19-7

Basic information

• Product Name: FMOC-D-PIPECOLIC ACID
• Synonyms: (D)-N-(9-FLUORENYLMETHYLOXYCARBONYL)PIPECOLIC ACID;(D)-N-FMOC-PIPECOLIC ACID;FMOC-(R)-PIPECOLINIC ACID;FMOC-(R)-(+)-PIPERIDINE-2-CARBOXYLIC ACID;FMOC-(R)-PIPERIDINE-2-CARBOXYLIC ACID;FMOC-D-PIP-OH;FMOC-D-PIC(2)-OH;FMOC-D-HOMOPRO-OH
• CAS NO: 105751-19-7
• Molecular Formula: C₂₁H₂₁NO₄
• Molecular Weight: 351.4
• Mol File: 105751-19-7.mol
• Article Data: 19

Chemical Properties

• Melting Point: 150-151℃
• Boiling Point: 561.6 °C at 760 mmHg
• Flash Point: 293.5 °C
• Appearance: /
• Density: 1.293 g/cm³
• Vapor Pressure: 1.89E-13mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: 2-8°C
• CAS DataBase Reference: FMOC-D-PIPECOLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-D-PIPECOLIC ACID(105751-19-7)
• EPA Substance Registry System: FMOC-D-PIPECOLIC ACID(105751-19-7)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-50/53
• Safety Statements: 26-36-61-60
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 105751-19-7(Hazardous Substances Data)

Usage

Description

FMOC-D-PIPECOLIC ACID, also known as N-(9-Fluorenylmethoxycarbonyl)-D-pipecolic acid, is a synthetic compound commonly used in the field of organic chemistry and pharmaceutical research. It is a derivative of pipecolic acid, featuring a 9-fluorenylmethoxycarbonyl (Fmoc) protecting group, which is crucial for its applications in peptide synthesis and other chemical reactions. The Fmoc group provides selectivity and stability, making FMOC-D-PIPECOLIC ACID a valuable reagent in various chemical processes.

Uses

Used in Pharmaceutical Research:
FMOC-D-PIPECOLIC ACID is used as a reactant for the racemic solid-phase preparation of human protease-activated receptor 2 (PAR2) agonists and antagonists. These compounds play a significant role in various physiological processes, including inflammation, pain, and blood clotting. The development of PAR2 agonists and antagonists can lead to novel therapeutic strategies for treating conditions such as asthma, chronic obstructive pulmonary disease (COPD), and inflammatory bowel disease (IBD).
Used in Analytical Chemistry:
FMOC-D-PIPECOLIC ACID serves as an analyte for urea-linked cinchona-calexarene hybrid type receptors in the chromatographic enantiomer separation of carbamate-protected amino acids. This application is essential for the purification and analysis of chiral compounds, which are crucial in the pharmaceutical industry due to their different biological activities and potential for improved drug efficacy and reduced side effects.
Used in Combinatorial Chemistry:
FMOC-D-PIPECOLIC ACID is employed as a combinatorial reactant for the assembly of alkylglycine library arrays using the SPOT (Synthetic Peptide On Tape) technique on cellulose membranes. This method allows for the identification of micromolar ligands for monoclonal antibodies, which can be used in the development of new drugs and therapeutic agents. The SPOT technique is a powerful tool for high-throughput screening and the discovery of novel bioactive compounds.

InChI:InChI=1/C21H21NO4/c23-20(24)19-11-5-6-12-22(19)21(25)26-13-18-16-9-3-1-7-14(16)15-8-2-4-10-17(15)18/h1-4,7-10,18-19H,5-6,11-13H2,(H,23,24)/t19-/m1/s1

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 15912-30-8 (2S)-2-piperidinecarboxylic acid L-tartrate 
• 88744-04-1 (9-fluorenyl)methyl pentafluorophenyl carbonate 
• 3105-95-1 pipecolinic acid 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 4043-87-2 pipecolic Acid 
• 102774-86-7 9-fluorenylmethyl N-succinimidyl carbonate 
• 15912-30-8 (R)-(+)-2-piperidinecarboxylic acid (+)-tartrate 
• 1723-00-8 (R)-(+)-pipecolic acid 
• 6940-78-9 4-chlorobutyl bromide 
• 136552-06-2 N-(N-(9-fluorenyl)methoxycarbonyl)-L-azetidine-2-carboxylic acid 

Downstream Products

• 86060-91-5 Fmoc-Pip-Pfp 
• 195202-02-9 (S)-1-(9H-fluoren-9-yl)methyl 2-((R)-1-(3-(2-tert-butoxy-2-oxo-ethoxy) phenyl)-3-(3,4-dimethoxyphenyl)propyl) piperidine-1,2-dicarboxylate 
• 507267-90-5 Z-Aib-Aib-Pip-Aib-Gly-OH 
• 195202-03-0 (S)-((R)-1-(3-(2-tert-butoxy-2-oxoethoxy)phenyl)-3-(3,4-dimethoxyphenyl)-propyl) piperidine-2-carboxylate 

Relevant articles and documents

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A series of 35 analogues of Shld with modifications in the A-residue and the C-residues were prepared and investigated for binding to FKBP and GFP accumulation in transgenic plants. The modifications investigated explored variations that were supposedly i

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