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Chemical Structure| 468061-05-4 Chemical Structure| 468061-05-4

Structure of H-cis-D-3-OH-Pro-OH·HCl
CAS No.: 468061-05-4

Chemical Structure| 468061-05-4

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Vodova, Milada ; Babini, Elena ; Soglia, Francesca ; Bordini, Martina ; Lioi, Martina ; Tengattini, Sara , et al.

Abstract: The stability of collagen, the most abundant protein in humans and many animals, is related to the hydroxylation of L-proline, a post-translational modification occurring at carbon 3 and 4 on its pyrrolidine ring. Collagens of different origins have shown different proline hydroxylation levels, making hydroxyprolines useful biomarkers in structure characterizations. The presence of two chiral carbon atoms, 3-hydroxyproline and 4-hydroxyproline, results in eight stereoisomers (four pairs of enantiomers) whose quantitation in collagen hydrolysates requires enantioselective analytical methods. Capillary electrophoresis was applied for the separation and quantitation of the eight stereoisomers of 3- and 4-hydroxyproline and D,L-proline in collagen hydrolysates. The developed method is based on the derivatization with the chiral reagent (R)-(-)-4-(3-Isothiocyanatopyrrolidinyl)-7-nitro-2,1,3-benzoxadiazole, enabling the use of a light-emitting diode-induced fluorescence detector for high sensitivity. The separation of the considered compounds was accomplished in less than 10 min, using a 500 mM acetate buffer pH 3.5 supplemented with 5 mM of heptakis(2,6-di-O-methyl)-β-cyclodextrin as the chiral selector. The method was fully validated and showed the adequate sensitivity for the application to samples of collagen hydrolysates. The analysis of samples extracted from chicken Pectoralis major muscles affected by growth-related myopathies showed different stereoisomer patterns compared to those from the unaffected control samples.

Keywords: capillary electrophoresis ; hydroxyprolines ; chiral separations ; collagen ; cyclodextrins ; derivatization ; fluorescent detection ; fast-growing chickens ; wooden breast ; spaghetti meat

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Product Details of [ 468061-05-4 ]

CAS No. :468061-05-4
Formula : C5H10ClNO3
M.W : 167.59
SMILES Code : O=C([C@@H]1NCC[C@@H]1O)O.[H]Cl
MDL No. :MFCD28398118
InChI Key :HHFGQFQJUWOFCN-RFKZQXLXSA-N
Pubchem ID :91800847

Safety of [ 468061-05-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501
 

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