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G Sarakinos

Publications and source records attributed to G Sarakinos.

5 recordsLinked to original sources

A practical new chiral controller for asymmetric Diels-Alder and alkylation reactions.

[formula: see text] The enantiomerically pure hydroxy sulfones (+)- and (-)-2 have been prepared from 1,2-epoxycyclohexane by a simple and practical procedure. The acrylate esters of these alcohols undergo BCl3-catalyzed Diels-Alder reactions with a variety of dienes at -78 to -55 degrees C in CH2Cl2 or C7H8 with high dienophile face selectivity (Table 1). The chiral esters so formed are readily cleaved with recovery of the controllers (+)- or (-)-2. Esters of (+)- and (-)-2 can be converted to Z-potassium enolates and alkylated with high face selectivity.

Alkylation↗

Simple and practical routes to enantiomerically pure 5-(trialkylsilyl)-2-cyclohexenones.

[reaction: see text] Enantiomerically pure chiral 5-silylated 2-cyclohexenones are easily prepared in high yield using as a key step kinetic resolution with a commercially available lipase. Fully active enzyme can be recovered very efficiently for reuse. The synthetic steps are outlined in Schemes 1 and 3. Enantiomerically pure 2-cyclohexenones such as 1 and 2 are versatile intermediates for the synthesis of a multitude of chiral targets by means of a variety of diastereoselective reactions such as those illustrated in Scheme 2.

Chromatography, High Pressure Liquid↗

Laminated three-dimensional biodegradable foams for use in tissue engineering.

A novel processing technique is reported to construct three-dimensional biodegradable polymer foams with precise anatomical shapes. The technique involved the lamination of highly-porous membranes of porosities up to 90%. Implants with specific shapes were prepared made of poly(L-lactic acid) and copolymers of poly(DL-lactic-co-glycolic acid) to evaluate feasibility. The biomaterials produced have pore morphologies similar to those of the constituent membranes. The pores of adjacent layers of laminated devices are interconnected, resulting in continuous pore structures. The compressive creep behaviour of multilayered devices is also similar to that of the individual layers. Recent discoveries from our group and others that organs and tissues can be regenerated and reconstructed, using cells cultured on synthetic biodegradable polymers, renders this method useful in creating polymer-cell graft for use in cell transplantation.

Biocompatible Materials↗

Cell seeding in porous transplantation devices.

Porous laminated discs of 1.35 cm diameter and thickness of 0.5 cm fashioned from biodegradable polymers were used as scaffolds for the transplantation of isolated cell populations. The distribution of cells seeded in these devices via injection was modelled with a system of dyed polymeric microparticles. Optimization of parameters related to device design and surgical injection conditions was carried out to maximize the device volume effectively employed in cell transplantation. The area of distribution on the top surface of each device was determined by image analysis techniques and used as a measure of the spatial distribution of injected particles. For poly(L-lactic acid) devices of porosity of 0.83 and median pore diameter of 166 microns seeded with 6 microns beads under standard injection conditions, the average surface area of distribution was 44.45% (+/- 3.36%). The device pore size was found to be a crucial determinant of particle distribution, whilst particle size in the range of 1-10 microns was not found to be important for the devices tested. Application of these results to the seeding of hepatocyte suspensions was made.

Animals↗

Dynamics of fibrovascular tissue ingrowth in hydrogel foams.

We have investigated and quantified the degree of fibrovascular tissue ingrowth in cylindrical poly(vinyl alcohol) (PVA) foams of 12.5 mm diameter, 5 mm thickness, and 71% porosity implanted in the mesentery of rats over a period of 25 days. Fibrovascular tissue penetrated the center of PVA foams 5 days postimplantation yet the void fraction available for cell seeding was 55% and the volume average pore diameter was 190 (+/- 39) microns. By 10 days postimplantation the void fraction had decreased to 32% and the volume average pore diameter was 121 (+/- 20) microns. As time elapsed fibrovascular tissue continued to expand and fill the remaining pore space. At 15 days postimplantation the void space was impractical for cell seeding and continued to decrease through the remainder of the study. Our data suggest that hydrogel foams with a polydispersed pore morphology can be prevascularized with adequate space for cell seeding as the volume of tissue penetrating the foam is limited by the smaller pores in the foam structure; however, available void space for cell seeding decreases with time.

Animals↗