2-Amino-1,3-propane diols: a versatile platform for the synthesis of aliphatic cyclic carbonate monomers

Venkataraman, S.; Veronica, Natalia; Voo, Zhi Xiang; Hedrick, James L.; Yang, Yi Yan

doi:10.1039/c3py00318c

Cited by 46 publications

(47 citation statements)

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“…71 Furthermore, the amino groups of serinol and AMPD are effective in selective reactions with esters and biscarbonates to form amides and carbamates without the protection of the hydroxyl groups. 72 The synthesis of the corresponding TMC analogues is relatively straightforward compared to that of others, and thus exploring the applications of the PTMC derivatives ( Figure 3F) is greatly expected. In addition to the reagents cited above, there are further commercially available substituted 1,3-diols.…”

Section: Incorporation Of Functional Side Chainsmentioning

confidence: 96%

“…Although no report has been published yet, some of the serinol-derived PTMC derivatives ( Figure 3E, F) can be potentially used as polymeric antimicrobials through quaternization and acidolysis of tert-butoxycarbonyl(Boc)-protected side chain affording ammonium salts. 72 Please do not adjust margins Please do not adjust margins Besides the modulation of the primary architecture of the cationic moiety, the introduction of biocompatible biomolecules, 216,218 supramolecular approach, 219 and hydrogelation 220 have also been surveyed to increase and broaden the antimicrobial properties with a low level of hemolytic properties ( Figure 10). In particular, the supramolecular approach raised the importance of the shape of antimicrobials upon the efficacy against some fungi.…”

Section: Antimicrobialmentioning

confidence: 99%

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Poly(trimethylene carbonate)-based polymers engineered for biodegradable functional biomaterials

2016

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Aliphatic polycarbonates have drawn attention as biodegradable polymers that can be applied to a broad range of resorbable medical devices. In particular, poly(trimethylene carbonate) (PTMC), its copolymers, and its derivatives are currently studied due to their unique degradation characteristics that are different from those of aliphatic polyesters. Furthermore, their flexible and hydrophobic nature has driven the application of PTMC-based polymers to soft tissue regeneration and drug delivery. This review presents the diverse applications and functionalization strategies of PTMC-based materials in relation to recent advances in medical technologies and their subsequent needs in clinical settings.

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Section: Incorporation Of Functional Side Chainsmentioning

confidence: 96%

Section: Antimicrobialmentioning

confidence: 99%

Poly(trimethylene carbonate)-based polymers engineered for biodegradable functional biomaterials

2016

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“…[16][17][18][19] Recent advances in transition-metal free organo-catalytic ROP allow controlled synthesis of polycarbonates. [16][17][18][19] Recent advances in transition-metal free organo-catalytic ROP allow controlled synthesis of polycarbonates.…”

Section: Polymer Synthesismentioning

confidence: 99%

Modular composite hydrogels from cholesterol-functionalized polycarbonates for antimicrobial applications

et al. 2015

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Micellar composite hydrogel systems represent a promising class of materials for biomolecule and drug delivery applications. In this work a system combining micellar drug delivery with supramolecular hydrogel assemblies is developed, representing an elegant marriage of aqueous hydrophobic drug delivery and next-generation injectable viscoelastic materials. Novel shear thinning and injectable micellar composite hydrogels were prepared using an amphiphilic ABA-type triblock copolymer consisting of a hydrophilic middle block and cholesterol-functionalized polycarbonates as the terminal hydrophobic blocks. Varying the concentration and relative hydrophobic-hydrophilic content of the amphiphilic species conferred the ability to tune the storage moduli of these gels from 200 Pa to 3500 Pa. This tunable system was used to encapsulate drugloaded polymeric micelles, demonstrating a straightforward and modular approach to developing micellar viscoelastic materials for a variety of applications such as delivery of hydrophobic drugs. These hydrogels were also mixed with cholesterol-containing cationic polycarbonates to render antimicrobial activity and capability for anionic drug delivery. Additionally, small-angle X-ray scattering (SAXS) and electron microscopy (EM) results probed the mesoscale structure of these micellar composite materials, lending molecular level insight to the self-assembly properties of these gels. The antimicrobial composite hydrogels demonstrated strong microbicidal activity against Gram-negative and Gram-positive bacteria, and C. albicans fungus. Amphotericin B (AmB, an antifungal drug)-loaded micelles embedded within the hydrogel demonstrated sustained drug release over 4 days and effective eradication of fungi. Our findings demonstrate that materials of different nature (i.e. small molecule drug or charged macromolecule) can be physically combined with ABA-type triblock copolymer gelators to form hydrogels for potential pharmaceutical application. Figure 2. SAXS spectra of gels formed with (A) ABA-2 gels in DI water with increasing polymer concentration from 4 to 12 wt.%;; (B) ABA-2, ABA-3, and ABA-4 12 wt. % concentration in DI water with varied cholesterol content and varied PEG hydrophilic segment molecular weights; (C) ABA-3 containing AB-micelles with polymer concentrations of 4 and 8 wt.%. All spectra are vertically offset for visual clarity. PEG-OH were purchased from Sigma-Aldrich [BioUltra; product numbers 95172poly(ethylene glycol) 20,000; LOT BCBF2828V and 94646 -poly(ethylene glycol) 35,000; LOT BCBD7453V]. Supplier provided molecular mass of as per certificate of analysis for the respective lots were used as such without any further cross verification.According to Sigma-Aldrich's lot specific certificate of analysis, these macroinitiators were reported to have molecular mass of 19611 and 28055 Da respectively (calculated from hydroxyl value). Amphotericin B (AmB) was purchased from Sigma-Aldrich.

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“…However, insofar as acetyl group [9][10][11][12], carbonate [6,13,14] and acetal [15] moieties, and other protecting groups in polyols tend to migrate or being involved in rearrangements to thermodynamically more favorable structures, the formation of the corresponding dioxane derivatives like 5 instead of 2 and 3 cannot be ruled out. Calculated energies of stable conformers of 2 and 5.…”

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confidence: 99%

Reaction of (2S,3S)-2-benzyloxybutane-1,2,4-triol with N,N′-carbonyldiimidazole

et al. 2015

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2S,3S)-2-Benzyloxybutane-1,2,4-triol reacted with N,N′-carbonyldiimidazole to give a mixture of the expected 1,2-carbonate and the corresponding bis-carbonate. Im = 1H-imidazol-1-yl.Cyclic carbonates are widely used as protecting and activating groups [1-3]. They are more stable than esters under both acid and base hydrolysis conditions. The 1,2-or 1,3-dihydroxy moiety in triols is usually protected by treatment with an appreciable excess of N,N′-carbonyldiimidazole.leads to selective hydrolysis of the latter to hydroxy carbonate B [4].While studying the reaction of (2S,3S)-2-benzyloxybutane-1,2,4-triol (1) with N,N′-carbonyldiimidazole, we have found that cyclic carbonate 2 generated from triol 1 [5] undergoes intermolecular bis-acylation in situ. In the reaction of 1 with a slight excess of N,N′-carbonyldiimidazole we obtained a mixture of carbonate 2 and bis-carbonate 3 at a ratio of ~3 : 2.5 in an overall yield of 56% (Scheme 1). The formation of 3 may be rationalized by esterification of a probable intermediate, activated N-acyl imidazole 4, with alcohol 2.The following factors were taken into account while assigning the structures of 2 and 3. It is known

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2-Amino-1,3-propane diols: a versatile platform for the synthesis of aliphatic cyclic carbonate monomers

Cited by 46 publications

References 46 publications

Poly(trimethylene carbonate)-based polymers engineered for biodegradable functional biomaterials

Poly(trimethylene carbonate)-based polymers engineered for biodegradable functional biomaterials

Modular composite hydrogels from cholesterol-functionalized polycarbonates for antimicrobial applications

Reaction of (2S,3S)-2-benzyloxybutane-1,2,4-triol with N,N′-carbonyldiimidazole

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