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[ CAS No. 73-32-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 73-32-5
Chemical Structure| 73-32-5
Structure of 73-32-5 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

Martina Lioi ; Sara Tengattini ; Roberto Gotti , et al. DOI:

Abstract: During collagen biosynthesis, proline is post-translationally converted to hydroxyproline by specific enzymes. This amino acid, unique to collagen, plays a crucial role in stabilizing the collagen triple helix structure and could serve as an important biomarker for collagen content and quality analysis. Hydroxyproline has four isomers, depending on whether proline is hydroxylated at position 4 or 3 and on whether the cis- or trans- conformation is formed. Moreover, as extensive hydrolysis of collagen is required for its amino acid analysis, epimerization may also occur, although to a lesser extent, giving a total of eight possible isomers. The aim of the present study was to develop a reversed-phase high-performance liquid chromatography-UV-mass spectrometry (RPLC-UV-MS) method for the separation and quantification of all eight hydroxyproline isomers. After the chiral derivatization of the hydroxyproline isomers with Nα-(2,4-dinitro-5-fluorophenyl)-L-valinamide (L-FDVA), to enable their UV detection, the derivatized diastereoisomers were separated by testing different C18 column technologies and morphologies and optimizing operative conditions such as the mobile phase composition (solvent, additives), elution mode, flow rate and temperature. Baseline resolution of all eight isomers was achieved on a HALO? ES-C18 reversed-phase column (150×1.5 mm, 2.7 μm, 160 ?) using isocratic elution and MS-compatible mobile phase. The optimized method was validated for the quantification of hydroxyproline isomers and then applied to different collagen hydrolysates to gain insight and a deeper understanding of hydroxyproline abundances in different species (human, chicken) and sources (native, recombinant).

Keywords: Collagen ; Amino acid analysis ; Hydroxyproline isomers ; Recombinant collagen ; Reverse phase chromatography ; Mass spectrometry

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Product Details of [ 73-32-5 ]

CAS No. :73-32-5 MDL No. :MFCD00064222
Formula : C6H13NO2 Boiling Point : -
Linear Structure Formula :H2NCH(CH(CH3)CH2CH3)COOH InChI Key :AGPKZVBTJJNPAG-WHFBIAKZSA-N
M.W : 131.17 Pubchem ID :6306
Synonyms :
Ile;isoleucine

Calculated chemistry of [ 73-32-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 35.44
TPSA : 63.32 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.29
Log Po/w (XLOGP3) : -1.72
Log Po/w (WLOGP) : 0.44
Log Po/w (MLOGP) : -1.82
Log Po/w (SILICOS-IT) : -0.15
Consensus Log Po/w : -0.39

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.63
Solubility : 557.0 mg/ml ; 4.25 mol/l
Class : Highly soluble
Log S (Ali) : 0.9
Solubility : 1050.0 mg/ml ; 8.02 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.14
Solubility : 96.1 mg/ml ; 0.733 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.65

Safety of [ 73-32-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 73-32-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 73-32-5 ]

[ 73-32-5 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 73-32-5 ]
  • [ 24629-25-2 ]
YieldReaction ConditionsOperation in experiment
4.5 g With lithium aluminium tetrahydride; In tetrahydrofuran; for 20h;Reflux; Inert atmosphere; L-Isoleucinol 3: L-Isoleucinol was prepared following a reported procedure61 with slight modifications. Under nitrogen, 2.5 equiv of Lithium aluminium hydride (7.2 g, 0.19 mol) was stirred in dry THF (120 mL). Then L-isoleucine (10?g, 0.08?mol) was added in portions and the suspension was refluxed for 20?h. After cooling to room temperature, ethyl acetate was added and the reaction mixture was poured carefully to concentrated sodium hydroxide solution. The organic layer was extracted with water and dried with sodium sulphate. 4.5?g of yellow liquid isoleucinol was obtained after removing the solvents. The product was used without further purification. 1H NMR (400?MHz, CDCl3): delta 0.75-0.90 (6H, m), 1.01-1.17 (1H, m), 1.22-1.36 (1H, m), 1.37-1.50 (1H, m), 2.48 (2H, br s), 2.50-2.65 (1H, m), 3.19-3.29 (1H, m), 3.57 (1H, dd, J?=?3.27, 10.64?Hz) ppm.
  • 2
  • [ 27243-15-8 ]
  • [ 73-32-5 ]
  • [ 67253-30-9 ]
  • 3
  • [ 73-32-5 ]
  • (2S,3S)-(+)-2-amino-3-methylpentan-1-ol N-borane [ No CAS ]
  • [ 24629-25-2 ]
  • 4
  • [ 73-32-5 ]
  • [ 24629-25-2 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride; In tetrahydrofuran; General procedure: The compounds were prepared in a similar manner as described before9. The chiralamino acid was reduced to the amino alcohol by treatment with LiAlH4 in THF. Thereaction was quenched with water. The solid was filtered off and the filtrate was driedover anhydrous sodium sulfate. The solvent was removed under reduced pressure togive the crude product. Subsequent treatment of the crude product with TsCl andK2CO3 in MeCN afforded pure chiral aziridines.
  • 5
  • pembamide [ No CAS ]
  • [ 56-41-7 ]
  • [ 72-18-4 ]
  • [ 2480-23-1 ]
  • [ 73-32-5 ]
  • [ 4125-98-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; at 110℃; for 18h; Compound 1 (0.4 mg) was hydrolyzed with 0.5 mL of 6N HCl at 110 C for 18 h. Excess aqueous HCl was removed under a N2 stream.
  • 6
  • [ 1721-26-2 ]
  • [ 73-32-5 ]
  • ethyl 6-(sec-butyl)-2-methylnicotinate [ No CAS ]
  • ethyl 2-methyl-6-(2-methylbutanoyl)nicotinate [ No CAS ]
  • 7
  • auxarthride B [ No CAS ]
  • [ 72-18-4 ]
  • [ 3060-46-6 ]
  • [ 73-32-5 ]
  • [ 2566-30-5 ]
  • 8
  • [ 73-32-5 ]
  • [ 85822-16-8 ]
  • ((4-formylphenyl)sulfonyl)-L-isoleucine [ No CAS ]
  • 9
  • amantamide [ No CAS ]
  • [ 72-18-4 ]
  • [ 61-90-5 ]
  • [ 73-32-5 ]
  • [ 3060-46-6 ]
  • [ 56564-52-4 ]
  • [ 56-40-6 ]
  • [ 88930-14-7 ]
  • [ 147-85-3 ]
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