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[ CAS No. 147-85-3 ] {[proInfo.proName]}

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Chemical Structure| 147-85-3
Chemical Structure| 147-85-3
Structure of 147-85-3 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 147-85-3 ]

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Product Citations

Product Citations      Expand+

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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Chandra, Shambhu Deo ; Gunasekera, Shanal ; Noichl, Benjamin Philipp , et al. DOI:

Abstract: We report a streamlined synthesis of (2S,3R,4R)-4,5-dihydroxy isoleucine (DHIle), an amino acid found in α-amanitin, which appears to be critical for toxicity. This synthetic route is transition metal-free and enables the production of significant quantities of DHIle with suitable protection for use in peptide synthesis. Its incorporation into a cytotoxic amatoxin analog is reported.

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Chao, Chi Bong Eric ; Pham, Quoc Hoang ; Richardson, Christopher , et al. DOI: PubMed ID:

Abstract: Diastereoselective Pd-catalyzed (3+2) and (4+2) cycloaddition reactions of sulfamidate imine-derived 1-azadienes with zwitterionic N-dipoles derived from 1-tosyl-2-vinylaziridine and 4-vinylbenzoxazinone have been developed. These reactions provide highly functionalized azaspirocycles featuring three contiguous stereocenters. The sulfonyl imine moiety of the cycloadducts can be fully reduced to access valuable β-amino alcohols.

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Product Details of [ 147-85-3 ]

CAS No. :147-85-3 MDL No. :MFCD00064318
Formula : C5H9NO2 Boiling Point : -
Linear Structure Formula :(C4H8N)C(O)OH InChI Key :-
M.W : 115.13 Pubchem ID :-
Synonyms :
(S)-(–)-Proline;NSC 46703;Prolina;HSDB 1210;FEMA No. 3319;CB 1707;Proline;L-(–)-Proline

Calculated chemistry of [ 147-85-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 32.52
TPSA : 49.33 ?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) : -8.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.84
Log Po/w (XLOGP3) : -2.5
Log Po/w (WLOGP) : -0.56
Log Po/w (MLOGP) : -2.59
Log Po/w (SILICOS-IT) : 0.22
Consensus Log Po/w : -0.92

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 1.09
Solubility : 1410.0 mg/ml ; 12.2 mol/l
Class : Highly soluble
Log S (Ali) : 2.01
Solubility : 11700.0 mg/ml ; 102.0 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.13
Solubility : 85.7 mg/ml ; 0.745 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 147-85-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 147-85-3 ]

* 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.

  • Upstream synthesis route of [ 147-85-3 ]
  • Downstream synthetic route of [ 147-85-3 ]

[ 147-85-3 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 110-16-7 ]
  • [ 147-85-3 ]
  • [ 406213-94-3 ]
  • [ 76095-16-4 ]
Reference： [1] Organic letters, 2002, vol. 4, # 23, p. 4005 - 4008
  • 2
  • [ 147-85-3 ]
  • [ 119020-03-0 ]
Reference： [1] Tetrahedron Letters, 1991, vol. 32, # 49, p. 7183 - 7186
  • 3
  • [ 147-85-3 ]
  • [ 22348-31-8 ]
Reference： [1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 8-9, p. 691 - 704
  • 4
  • [ 147-85-3 ]
  • [ 157115-85-0 ]
Reference： [1] European Journal of Medicinal Chemistry, 1996, vol. 31, # 2, p. 151 - 157
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