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Chemical Structure| 147-85-3 Chemical Structure| 147-85-3
Chemical Structure| 147-85-3

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CAS No.: 147-85-3

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H-Pro-OH is one of the common amino acids that involved in the synthesis of proteins.

Synonyms: (S)-(–)-Proline; NSC 46703; Prolina

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Martina Lioi ; Sara Tengattini ; Roberto Gotti ; Francesca Bagatin ; Stefano Galliani ; Gabriella Massolini , et al.

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 ; Patrick, Brian O ; Perrin, David M ;

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 ; Pyne, Stephen G ; Hyland, Christopher JT ;

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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Alternative Products

Product Details of H-Pro-OH

CAS No. :147-85-3
Formula : C5H9NO2
M.W : 115.13
SMILES Code : O=C(O)[C@H]1NCCC1
Synonyms :
(S)-(–)-Proline; NSC 46703; Prolina
MDL No. :MFCD00064318

Safety of H-Pro-OH

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Application In Synthesis of H-Pro-OH

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

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