Fmoc-D-homoproline
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Fmoc-D-homoproline

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Category
Cyclic Amino Acids
Catalog number
BAT-007417
CAS number
101555-63-9
Molecular Formula
C21H21NO4
Molecular Weight
351.40
Fmoc-D-homoproline
IUPAC Name
(2R)-1-(9H-fluoren-9-ylmethoxycarbonyl)piperidine-2-carboxylic acid
Synonyms
Fmoc-D-HomoPro-OH; Fmoc-D-pipecolic acid; Fmoc D HomoPro OH
Appearance
White powder
Purity
≥ 98% (HPLC)
Density
1.293 g/cm3
Melting Point
152-158 °C
Boiling Point
561.6°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/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
InChI Key
CKLAZLINARHOTG-LJQANCHMSA-N
Canonical SMILES
C1CCN(C(C1)C(=O)O)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
1.Chiral separation of the clinically important compounds fucose and pipecolic acid using CE: determination of the most effective chiral selector.
Hadjistasi CA1, Stavrou IJ, Stefan-Van Staden RI, Aboul-Enein HY, Kapnissi-Christodoulou CP. Chirality. 2013 Sep;25(9):556-60. doi: 10.1002/chir.22170. Epub 2013 Jun 11.
In this study, simple electrophoretic methods were developed for the chiral separation of the clinically important compounds fucose and pipecolic acid. In recent years, these analytes, and particularly their individual enantiomers, have attracted considerable attention due to their role in biological functions and disorders. The detectability and sensitivity of pipecolic acid and fucose were improved by reacting them with fluorenylmethyloxycarbonyl chloride (FMOC-Cl) and 5-amino-2-naphthalene-sulfonic acid (ANSA), respectively. The enantioseparation conditions were optimized by initially investigating the type of the chiral selector. Different chiral selectors, such as polymeric surfactants and cyclodextrins, were used and the most effective ones were determined with regard to resolution and analysis time. A 10-mM β-cyclodextrin was able to separate the enantiomers of ANSA-DL-fucose and the polymeric surfactant poly(sodium N-undecanoyl-LL-leucine-valinate) was able to separate the enantiomers of FMOC-DL-pipecolic acid, with resolution values of 3.
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