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[ CAS No. 5405-40-3 ] {[proInfo.proName]}

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Chemical Structure| 5405-40-3
Chemical Structure| 5405-40-3
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Product Citations

Product Citations      Expand+

Jahan, Samin ; Doyle, Catherine ; Ghimire, Anupama , et al. DOI: PubMed ID:

Abstract: Proteins are biomols. with potential applications in agriculture, food sciences, pharmaceutics, biotechnol., and drug delivery. Interactions of hydrophilic and biocompatible polymers with proteins may impart proteolytic stability, improving the therapeutic effects of biomols. and also acting as excipients for the prolonged storage of proteins under harsh conditions. The interactions of hydrophilic and stealth polymers such as poly(ethylene glycol), poly(trehalose), and zwitterionic polymers with various proteins are well studied. This study evaluates the mol. interactions of hydrophilic and optically active poly(vitamin B5 analogus methacrylamide) (poly(B5AMA)) with model proteins by fluorescence spectroscopy, NMR (NMR) spectroscopy, and CD (CD) spectroscopy anal. The optically active hydrophilic polymers prepared using chiral monomers of R-(+)- and S-(-)-B5AMA by the photo-iniferter reversible addition fragmentation chain transfer (RAFT) polymerization showed concentration-dependent weak interactions of the polymers with bovine serum albumin and lysozyme proteins. Poly(B5AMA) also exhibited a concentration-dependent protein stabilizing effect at elevated temperatures, and no effect of the stereoisomers of polymers on protein thermal stability was observed NMR anal., however, showed poly(B5AMA) stereoisomer-dependent changes in the secondary structure of proteins.

Keywords: chiral materials ; protein-polymer interactions ; antifouling ; protein stabilizing

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Combita, Diego ; Pamunuwegedara, Randima ; Ahmed, Marya DOI:

Abstract: Chiroptical polymers are interesting due to diverse applications in the field of chromatog., biomedicines, and catalysis. This study describes the synthesis of new types of optically active polymers of vitamin B5 analogous methacrylamide (B5AMA) using a photoiniferter polymerization approach at ambient temperatures Enantiomers of B5AMA monomer ((R) and (S)) were prepared by the ring opening method and were characterized for their optical activity. The monomers were then polymerized by a photoiniferter polymerization approach using two different thiocarbonylthio (TCT) compounds as iniferters. Both TCTs showed controlled polymerization of B5AMA enantiomers and yielded polymers of opposite optical rotation. The enantiomeric polymers of B5AMA exhibited a complementary mirror-image Cotton effect to each other in the CD (CD) spectra, and 13C NMR anal. revealed the formation of syndiotactic polymer structures. To the best of our knowledge, this is the first study that depicts the successful synthesis of optically active macromols. by a photoiniferter polymerization approach.

Keywords: enantiomers ; photoiniferter polymerization ; polymer tacticity ; optically active polymers ; random coil structure ; pendant group chirality

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Product Details of [ 5405-40-3 ]

CAS No. :5405-40-3 MDL No. :MFCD00216625
Formula : C6H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :SERHXTVXHNVDKA-SCSAIBSYSA-N
M.W : 130.14 Pubchem ID :736053
Synonyms :

Calculated chemistry of [ 5405-40-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 31.03
TPSA : 46.53 ?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) : -6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.31
Log Po/w (XLOGP3) : 0.46
Log Po/w (WLOGP) : -0.07
Log Po/w (MLOGP) : 0.0
Log Po/w (SILICOS-IT) : 0.78
Consensus Log Po/w : 0.5

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.94
Solubility : 15.1 mg/ml ; 0.116 mol/l
Class : Very soluble
Log S (Ali) : -1.01
Solubility : 12.8 mg/ml ; 0.0987 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.54
Solubility : 37.6 mg/ml ; 0.289 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.17

Safety of [ 5405-40-3 ]

Signal Word:Danger Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H303-H318 Packing Group:N/A
GHS Pictogram:
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Technical Information

? Acyl Group Substitution ? Appel Reaction ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bouveault-Blanc Reduction ? Bucherer-Bergs Reaction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Catalytic Hydrogenation ? Chugaev Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Ester Cleavage ? Fischer Indole Synthesis ? Grignard Reaction ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Jones Oxidation ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? Martin's Sulfurane Dehydrating Reagent ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mitsunobu Reaction ? Moffatt Oxidation ? Oxidation of Alcohols by DMSO ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Alcohols ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Prins Reaction ? Reactions of Alcohols ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions with Organometallic Reagents ? Reformatsky Reaction ? Ritter Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Sharpless Olefin Synthesis ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Swern Oxidation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction
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