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Polymer Discovery Via Microfluidic Enzymatic Synthesis. Prof. Peter Y. Wong Prof. David Kaplan Tufts University - Medford, MA October 3, 2006. Biochemical Science. Synthesis 1990-. Polymer science 1970-. Enzyme. Microsystems Technology. Mechanical. Electronics. Micro-fabrication.

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polymer discovery via microfluidic enzymatic synthesis

Polymer Discovery Via Microfluidic Enzymatic Synthesis

Prof. Peter Y. Wong

Prof. David Kaplan

Tufts University - Medford, MA

October 3, 2006

overview

Biochemical Science

Synthesis 1990-

Polymer science 1970-

Enzyme

Microsystems

Technology

Mechanical

Electronics

Micro-fabrication

Engineering

Overview
  • Markets
  • Needs
  • Problems
  • Solution
  • Team
  • Next Steps
  • Summary
many markets
Many Markets
  • Any market that benefits from new biochemicals
  • Improved Foods
    • Additives, Modification, Nutrition
  • Green Chemistry
    • Agricultural, Packaging, Analysis
  • New Medicines
    • Topical, Digested, Structural
markets needs vs wants
Markets Needs vs.Wants
  • New products
    • Better
    • Faster
    • Cheaper
    • Differentiated
  • Macro and Micromolecules needed
    • New material
    • New processes
  • Focus on new polymers and processes
problems and risks
Problems and Risks
  • Current Polymer Discovery Process
    • Long time with process and people
    • High costs and large resources needed
    • FDA, EPA stringent regulations
    • Limited research to commercialization
  • Alternate Approaches
    • Nanoscience/technologies - far in future?
    • Biomimetics/Bioinspiration - hit or miss?
    • Microengineering/fluidics - scalability?
our solution
Our Solution
  • Achieve “Green ( ) Polymer Chemistry” through
    • Enzymatic Synthesis and
    • Microfluidics
  • Enzymatic polymerizations can produce products
    • via mild reaction conditions w/o toxic reagents
    • in an environmentally friendly synthetic process
    • that can be scaled from microscale to macroscale
  • Target macromolecules include
    • polysaccharides, polyesters, polycarbonates, poly(amino acid)s, polyaromatics, and/or vinyl polymers.
microfluidic enzymatic cascade

Monomer

Enzyme 1

Natural antioxidant

Enzyme 2

Antioxidant Polymer

Microfluidic Enzymatic Cascade
  • Universal Lab-On-Chip is very far away
  • Application Specific Integrated Microfluidic (ASIM) device
  • Example ASIM –
    • produce vitamin C enriched polymers (PMMA) polymer
    • has both scientific and market value.
pmma polymer
PMMA Polymer
  • Disruptive Technology in Packaging
    • Vitamin C enriched polymers can replace butylated hydroxy anisole (BRA) and butylated hydroxy toluene (BHT) - FDA limits conc. To 0.02%.
  • New Topical Medicine
    • Antioxidants are considered important in reducing aging-related phenomena by providing protection against free radicals.
  • Nutraceutical Supplementation
    • Ascorbic acid may have an overall positive impact on public health because humans lack the ability to synthesize vitamin C
slide9
ASIM
  • Goals:
  • Two enzymatic cascade reactions to produce PMMA
  • low cost devices made of poly(dimethylsiloxane) (PDMS)
  • efficient method to optimize process with external controls
translation from abstract to hardware
Translation from Abstract to Hardware

ascorbic acid

monomer

AA-Monomer

AA- Ascorbic Acid

MMA- Methyl Methacrylate

PMMA- Poly (Methyl Methacrylate)

P-AA-MMA – Ploy L-Ascorbic Methyl Methacrylate

HRP – Horse Radish Peroxidase

lipase

HRP

: hydrogen

peroxide

ascorbic acid

Antioxidant polymer

monomer

:

:

Input

Input

: hydrogen

Input

Input

ascorbic acid

ascorbic acid

HRP

peroxide

#1

#2

:

:

:

:

Input

Input

Check Valve

Output

Output

Reaction Vessel #2

Reaction Vessel #1

Reaction Vessel #1

monomer

polymer

in solvent

in solvent

AA-Monomer

P-AA-MMA

AA-Monomer

React with lipase

React with

HRP

Hydrogen peroxide

:

:

unreacted

unreacted

Output

Output

:

:

unreacted

unreacted

Output

Output

lipase

hydrogen peroxide

hydrogen peroxide

ascorbic acid

ascorbic acid

improved version
Improved Version

1

Stage I Enzymatic Transesterification

Synthesis L-Ascrbyl Methyl methacrylate

Reaction vessel 1

50C<reaction temp <60C,

45 min.<reaction time<60 min.

Flow rate<0.01 ml/min.

2

Stage II HRP Polymerization L-Ascrbyl Methylmethacrylate

Reaction vessel 2

60 min.<reaction time<90 min.

20 min.<shaking time<30 min.

Flow rate<0.01 ml/min.

Function driven

Step

Material

Quantity used

Step

Material

Quantity

used

2,6-di-tert-butyl-4-methylphenol, Dioxane.

Functional

Substrate

(G1.1)

L-ascorbic acid

(AA)+50% Diox.

150mg,

0.852 mM

Mix1

(G2.1) w/G2.2

L-Ascrbyl methylmethacrylate

~0.02 g 0.082 mM

Ascorbic

acid, Dioxane

1st Vessel

>50C

2,2,2-trifluoroethyl methacrylate

0.182 mL, 1.278 mM

Tetrahydrofuran(solvent)

(THF) N2 flushed

0.11 ml

Initiator

A

B

2nd Vessel

HRP

1.6mg/

0.05ml

C

TFM, Diox.

Lipase,

1.5mlx2

anhydrous Dioxane

Dissolve

(G2.2)

water

2 ul

D

HRP,THF

Enzyme

(G1.2)

Antarctica lipase

(free)+ 40% Diox.

12.5mg

Hydrogen Peroxide

9.3ul

Hydrogen

peroxide

E

AA_PMMA,

/PMMA/

2.5mg

Anti-poly

60C (G1.3)

2,6-di-tert-butyl-4-methylphenol

+10% Diox.

Mix 2

2 hours

(G2.3) Shaking 1 hr

2,4-pentanedione

(trigger)

1.77ul

Vessel 1 L-Ascrbyl Methyl methacrylate

(AA-MMA) (G 1)

Vessel 2 Poly L-Ascorbyl Methyl methacrylate

(P-AA-MMA) (G.2)

asim manufacturing
ASIM manufacturing
  • DRIE Si wafer
  • PDMS Casting
  • Thermal Plasma Bonding to glass slide
  • Embed fluid connectors

PDMS on SI

PDMS on Glass slide

external hardware

Pneumatic controlling

Micrometer

Sample loading

Syringes

External Hardware
chemical analysis

Repeat unit

Signal strength

Macro

Molecular weight/ charge

Repeat unit

Micro

Chemical Analysis
  • Macro vs. Micro comparison with MALDI-TOF
  • Need purification but polymer exists
slide15
Team
  • David Kaplan - expertise in enzymatic reactions
  • Peter Wong - expertise in microfluidics
  • Jin Zou - PhD graduate in Mechanical Engineering
  • Martin Son - Tufts Technology Transfer Office
  • Tufts Capabilities:
    • Enzymatic synthesis research, development, and production
    • ASIM - Microfluidic design, analysis, and fabrication
    • Polymer discovery program – design of experiments and testing
next steps
Next Steps
  • Identify 2 to 3 market products to tackle
    • 2 months
  • Initial description of enzymatic synthesis process
    • 2 months
  • Convert preliminary patent application to full application with these examples of synthesis
    • 1 month
  • Develop next generation of ASIM devices for those specific market products
    • 6 months
  • Develop new polymer products
    • 6 months
  • Partner with companies to develop new polymers for their markets
summary
Summary
  • Food/Medicine/Biochem Markets need advantages of new polymers
  • Microfluidic Enzymatic Synthesis
    • Make custom polymers
    • Faster, cheaper discovery
    • Scalable to mass production
  • Need partners and funding to
    • do market analysis,
    • help secure IP,
    • develop small number of prototypes, and
    • expand to market
  • Contact Martin.Son@tufts.edu