From Glucose to Polymers: A Continuous Chemoenzymatic Process

Article abstract of DOI:10.1002/anie.202006468

Efforts to synthesize degradable polymers from renewable resources are deterred by technical and economic challenges; especially, the conversion of natural building blocks into polymerizable monomers is inefficient, requiring multistep synthesis and chromatographic purification. Herein we report a chemoenzymatic process to address these challenges. An enzymatic reaction system was designed that allows for regioselective functional group transformation, efficiently converting glucose into a polymerizable monomer in quantitative yield, thus removing the need for chromatographic purification. With this key success, we further designed a continuous, three-step process, which enabled the synthesis of a sugar polymer, sugar poly(orthoester), directly from glucose in high yield (73 % from glucose). This work may provide a proof-of-concept in developing technically and economically viable approaches to address the many issues associated with current petroleum-based polymers.

Full text of DOI:10.1002/anie.202006468

A Journal of the Gesellschaft Deutscher Chemiker
Angewandte
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Accepted Article
Title: From Glucose to Polymers----A Continuous Chemoenzymatic
Process
Authors: Wenjun Du, Sampa Maiti, Saikat Manna, Nicholas Banahene,
Lucynda Pham, Zhijie Liang, Jun Wang, Yi Xu, Reuben
Bettinger, John Zientko, and Aaron Esser-Kahn
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To be cited as: Angew. Chem. Int. Ed. 10.1002/anie.202006468
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From Glucose to Polymers----A Continuous Chemoenzymatic
Process
Sampa Maiti,a Saikat Manna,b Nicholas Banahene,a Lucynda Pham,a Zhijie Liang,a,c Jun Wang,a Yi Xu,a
Reuben Bettinger,a John Zientko,a Aaron P. Esser-Kahnb and Wenjun Dua*
[a]
S. Maiti, N. Banahene, L. Pham, Z. Liang, J. Wang, Y. Xu, R. Bettinger, J. Zientko, W. Du.
Department of Chemistry and Biochemistry, Science of Advanced Materials.
Central Michigan University
Mount Pleasant, Michigan 48859, United States
E-mail: du1w@cmich.edu
[b]
[c]
S. Manna, A. P. Esser-Kahn
Pritzker School of Molecular Engineering
The University of Chicago
Chicago, Illinois 60637, United States
Z. Liang
Current address: Department of Wound Repair Surgery,
The Fifth Affiliated Hospital of Guangxi Medical University & The First People’s Hospital of Nanning,
Nanning, China, 530000
Supporting information for this article is given via a link at the end of the document.
Abstract: Aiming for sustainable development, the syntheses of
degradable polymers from renewable resources are highly
encouraging. Unfortunately, such efforts are deterred by technical and
economic challenges; especially, the conversion of natural building
blocks to polymerizable monomers is inefficient, requiring multistep
synthesis and chromatographic purification. Herein we report a
chemoenzymatic process to address these challenges. In this work, a
novel enzymatic reaction system was designed, which allowed for
regioselective functional group transformation efficiently, converting
glucose to a polymerizable monomer in quantitative yield, thus
removing the need for chromatographic purification. With this key
success, we further designed a continuous, 3-step process, which
enabled the synthesis of a sugar polymer [sugar poly(orthoester)]
directly from glucose in high yield (73% from glucose). The work
expected to decrease further, and there are hopes that one day
this class of polymer may potentially replace certain polymers
arising from petroleum. Indeed, there is an increasing number of
studies on the synthesis of glucose-based polymers,[14-21] as a few
of these examples shown in Figure 1, including sugar polyamide
(IIIa),[15] sugar polycarbonate (IIIb)[16] and sugar poly(orthoester)
(IIIc).[19] However, in all of these studies, glucose must be first
converted to a polymerizable monomer, often, in a stepwise
manner, and requiring chromatographic purification in each step.
reported here may provide
a proof-of-concept in developing
technically and economically viable approaches to address the many
issues associated with current petroleum-based polymers.
With an annual production of ca. 400 million tons, polymers
play indispensable roles in our daily lives.[1-3] Yet, there are
environmental, economic, and social concerns, especially the
feedstock origins and end-of-use options. Currently, about 6% of
the world’s total petroleum output is used to produce polymers,[2]
and most of which are non-degradable, ending up in landfills, and
even in oceans. It is estimated that by 2050, there will be more
polymers in oceans than fish by mass.[4] Although there is no
panacea to address these complex problems, one promising
strategy is to develop polymers from natural building blocks,[3-6]
such as fatty acids[7, 8] and carbohydrates.[9, 10] However, despite
their abundance, converting pristine building blocks to
polymerizable monomers has been challenging; primarily due to
the need for multistep chemical synthesis and chromatographic
purification in each step, current syntheses are neither readily
scalable nor economically viable.
Figure 1. Examples of monomers (IIa-IIc) derived from glucose (I); and the
corresponding sugar polymers (IIIa-IIIc).
We were very interested in the sugar orthoester linkage
(Figure 1, structure IIIC), which exhibited favorable
biocompatibility that may enable further development as
biomaterials.[22] From the perspective of polymer degradation, the
orthoester was highly acid-sensitive and could be conveniently
degraded into non-toxic glucose derivatives under acidic
conditions.[19, 22] For example, at pH = 5, the half-life of the sugar
poly(orthoester) was only 0.6 h, allowing for efficient degradation
without the use of toxic reagents or energy input for
Amongst the many natural building blocks, glucose is one of
the most readily available, with the current price of roughly $0.4-
22]
degradation.[19,
However, despite these advantages, the
synthesis of the polymer, like every other sugar polymer reported
in the literature, was inefficient and tedious, involving many
$0.6/kg.[11] With the advancement in new bioprocesses that use
cellulose/lignocellulose as the feedstock;[12,
the price is
13]
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selective protection and deprotection steps in the preparation of a
polymerizable monomer.[19, 23]
To address this issue, we then conceived a system to “lock”
the water molecule. In this context, highly hydrophilic polymers,
such as alginate, [29] with the capability to “lock” water molecules
through a massive number of hydrogen bonding, may prevent the
hydrolysis. Therefore, we fabricated enzyme-encapsulated
alginate beads at varying concentrations (e.g. 2.0 g lipase in 10.0
mL of 2% alginate solution) using CaCl2 or BaCl2 solutions (2%).
Unfortunately, this strategy did not work, either. Possibly, within
this system, there was sufficient freedom for water movement due
to alginate’s egg-box gelling mechanism.[30, 31] With this in mind,
we next sought unconventional methods, such as using an
organic solvent, e.g. tetrahydrofuran (THF), acetone, and
methanol as the gelling agent. The less polar organic solvent
(compared to alginate) may push alginate, as well as water
molecules to pack tightly to form a stable gel.[32] In such a case,
we envisioned that there would be little freedom for water
movement, creating a “water locking solid system” (WLSS).
In light of this, enzymatic reactions, which are especially
advantageous for chemo- and regioselective functional group
transformations, have attracted our attention. We hypothesized
that by applying a right enzymatic reaction and condition, it would
greatly simplify the synthesis. Furthermore, if high conversion
could be obtained, e.g. quantitative conversion, it may also allow
for the removal of the need for chromatographic purification,
affording a highly efficient and even a continuous synthesis that
could potentially be economically-viable. With this goal, herein we
report a highly efficient chemo-enzymatic process to synthesize
sugar polymers directly from naturally occurring glucose.
To apply an enzymatic reaction, we first converted glucose (1)
to a monomer precursor (2), of which, the 6-OAc can then be
enzymatically deprotected to give the monomer (Scheme 1).
There have been studies on the synthesis of 2, e.g. from glucosyl
hemiacetal,[24], or glucose pentaacetate.[25] However, these
methods did not give 100% conversion, and consequently
required further purification. Herein, we designed an acetyl
halide/H2SO4/alumina system that could achieve the quantitative
synthesis. Under this condition, glucose was first converted to
glucose pentaacetate, following that the anomeric –OAc was
transformed to an anomeric halide, giving compounds 2a/2b
(Scheme 1) quantitatively, without any detectable by-product(s)
(Figure 3A and SI for details).
Thereby, lipase from varying sources (Aspergillus niger,
Aspergillus oryzae, Candida rugosa, and porcine pancreas) were
suspended in alginate solution (2% in phosphate buffer) and was
subsequently added to the organic solvent through a syringe
pump (at the rate of ca. 1 mL/min.). However, THF, acetone, and
methanol did not give stable WLSS, possibly, the enzyme may
adversely affect the packing between each alginate chains.
Fortunately, when 1,4-dioxane was used, stable and robust
WLSS beads were successfully fabricated. By changing the
gauge of the syringe needle, varying sizes of the beads could be
obtained. We later determined that beads of 0.5 mm ± 0.2 mm
provide both good handling (e.g. allow for easy cannulation in the
later step), high loading efficiency (66%) and loading capacity (40%
by mass) (Figures 2A, 2B and SI for details of the protocol and
measurement). The high loading capacity is essential in terms of
providing high enzyme/substrate ratio, thereby high reaction
efficiency.
With this success, we then tested its “water locking” and catalytic
capability. We envisioned that the pre-formed enzyme
encapsulated beads may be suspended in an organic solvent
which would provide good solubility to help transport the substrate
and the product in and out (of the beads), accomplishing the
regioselective 6-OAc deprotection, as schematically illustrated in
Figure 2A.
Scheme 1. The synthesis of sugar polymer 4 (same structure as that of IIIc
shown in Figure 1) from glucose (1).
With 2a/2b in hand, we were excited to explore the enzymatic
reaction. A variety of lipase has been reported to selectively
deprotect the 6-OAc of glucose derivatives (e.g. glucose
pentaacetate) with yields in the range of 80%-95%.[26-28]
Encouraged by these results, we first tested the deprotection of
compound 2a using lipase from Candida rugosa. However, when
the reaction was performed in THF/water (50/50, v/v), the
anomeric –Br was quickly hydrolyzed, e.g. within minutes
(determined by NMR analysis). The rate of hydrolysis was much
faster than that of 6-OAc deprotection, resulting in an undesired
by-product. Reducing the water content to 20% did not mitigate
this issue. Realizing that glycosyl bromide was highly sensitive to
hydrolysis, we then employed a more stable glucosyl chloride
precursor (2b, Scheme 1). Unfortunately, significant hydrolysis
was still observed, although at a much slower rate (ca. 20%
hydrolysis within 1 hour). Other efforts have been invested to
optimize the conditions, including using other sources of lipase
and varying the pH values. However, glycosyl halides are
extremely sensitive to hydrolysis and these efforts failed to solve
the problem.
Figure 2. A) Schematic illustration of the enzymatic reaction system, wherein
WLSS was suspended in 1,4-dioxane; compounds 2a or 2b were introduced to
the solution, transported into the beads wherein it was subject to 6-OAc
deprotection. B) Camera photo images of the enzyme-encapsulated WLSS
hydrogel beads, with sizes of 0.5 mm ± 0.2 mm; C) Kinetic study of the 6-OAc
deprotection of 2b (to give 3b) using WLSS system; the conversion values were
calculated from NMR analysis (Figure S8).
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After determining successful polymerization (by NMR and
GPC), the solvent was removed by VAVES; and the sugar
polymer was precipitated in a mixture solvent of methanol/water,
giving a polymer at 73% yield (based on glucose). The
synthesized polymer 4 was structurally identical to that reported
before[19] (Figure 3C), indicating a successful synthesis.
Not surprisingly, within this WLSS reaction system, there was
insignificant hydrolysis for 2a (ca. 10% hydrolysis after 3 h); and
essentially no detectable hydrolysis for 2b even after 15 h reaction,
indicating a successful “lock” of the water molecules. It should be
noted that many factors could also affect the efficiency and
regioselectivity, including the source of enzyme,[33] and pH
value.[34] After screening these parameters (see Table S1) we
found that at pH = 4, lipase from Candida rugosa performed the
best, giving 3b in quantitative yield, as shown in the reaction
kinetics and NMR analysis (Figures 2C, 3B and Figure S8). It is
worth mentioning that under this condition, the WLSS was very
robust, staying effective for up to 7 cycles, without noticeable loss
of enzyme activity. Furthermore, such a system could be scaled
up to 1.0 g, with about the same reaction efficiency.
These results were encouraging, we then envisioned that we
could possibly design a continuous process to produce the
polymer directly from glucose. As illustrated in Scheme 2, starting
in reaction vessel A, glucose was first added in a slurry of acetyl
chloride/alumina, with a few drops of conc. H2SO4 as a catalyst
(see SI for experimental details). After determining that glucose
had been completely converted to 2b (monitored by NMR
analysis), ethyl acetate (EtOAc) and water were added and the
top layer (EtOAc solution) was cannulated into reaction vessel B.
To accommodate a continuous process, the solvent should be
removed and recycled. Thereby we further developed a Vortex-
Assisted Vacuum Evaporation System (VAVES) [35] for in-vessel
solvent removal. This self-designed system, by creating a vortex
thereby increasing the surface area, allowed for removal of the
solvent (EtOAc) at a rate of about 50 mL/h (depending on the
airflow rate). After applying the VAVES, 2b was obtained as a
pure compound, without any trace of solvent or impurity, as
determined by NMR analysis (Figure 3A).
Figure 3. The 1H NMR spectra of A) precursor 2b; B) monomer 3b; and C)
sugar polymer 4. Both 2b and 3b were obtained by simple extraction of the
reaction mixture, without any chromatographic purification.
However, the monomer gave the sugar polymer with only
moderate molecular weights (MnGPC = 4.2 kDa, Figure 4A). Efforts
have been invested, e.g. increasing the reaction time/catalyst,
even the use of reverse-anomeric-effect (RAE)-enabling catalysts
such as DMAP (N,N-dimethylamino pyridine) or TPP (triphenyl
phosphine).[23] Unfortunately, these efforts did not improve the
molecular weights, possibly, due to the low reactivity of the
glycosyl chloride, (as compared to the glycosyl bromide monomer
3a, which gave a molecular weight of ca. 7.0 kDa[19]).
Even with a small molecular weight, the polymer exhibited a
o
high glass transition temperature (Tg = 93.3 C, Figure 4B). The
Tg value is comparable to other sugar polymers with much higher
molecular weights (e.g. 15-16 kDa).[17] The relatively high Tg
value is possibly due to the “locked“ sugar orthoester bond
resulting in a rigid backbone, and allowing for little rotation.
Additionally, the unique structure of the sugar unit may lead to
close stacking among the polymer chains, as reported in several
sugar molecules by Seeberger and co-workers.[36] On the other
hand, the polymer exhibited high thermal stability (stable at 180
oC, Figure 4C), indicating strong orthoester bonds within the
Scheme 2. Schematic illustration of the continuous chemoenzymatic process
to synthesize sugar polymer (4) directly from glucose.
In reaction vessel B, lipase-loaded WLSS beads suspended
in 1,4-dioxane were then added and the reaction mixture was
gently stirred (at ca. 250 rpm). The reaction was monitored by
TLC and NMR and the percentage of conversion was calculated
from the NMR analysis (Figure S8 and Figure 2C). After
determining that the reaction was completed, the solution was
cannulated into reaction vessel C, in which, the solvent (1,4-
dioxane) was removed through VAVES, leaving 3b as a pure
compound, as determined by NMR analysis (Figure 3B).
polymer. The two peaks suggested
a two-stage thermal
degradation, with the orthoester being degraded first, giving a
ketal structure, which degraded subsequently. The high Tg and
high thermal stability suggested that the polymer could be a useful
material, although its mechanical properties and processability
need to be further studied.
With monomer 3b in hand, we then tested the polymerization.
Pre-calculated amount of TBAI, DIPEA in DCM was added and
the polymerization was performed according to the literature.[19]
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Acknowledgments
A
We thank Dr. Benjamin Swarts, Dr. Mary Tecklenburg, and Dr.
David Ash for helpful discussion and thoughtful inputs in this
work. The authors gratefully acknowledge the National Science
Foundation [CHE-1413033] for the financial support.
Keywords: Polymer • synthesis, chemoenzymatic • continuous;
sustainable • glucose • renewable • poly(orthoester)
B
C
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In conclusion, we have successfully developed
a
chemoenzymatic synthesis of a sugar polymer using natural
building block glucose as the feedstock. We attributed the
success to the development of a WLSS enzymatic reaction
system that solved the hydrolysis problem during the enzymatic
reaction, allowing for efficient synthesis of a polymerizable
monomer. It should be noted that as most of the current enzymatic
reactions involve the use of water as a co-solvent, the
development of the WLSS could serve as a successful model to
expand the applications of enzymatic reactions to a large number
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currently underway in our lab.
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Entry for the Table of Contents (Please choose one layout)
Layout 1:
COMMUNICATION
From Glucose to
Polymers---A Continuous
Chemoenzymatic Process
Sampa Maiti,a Saikat Manna,b
Nicholas Banahene,a Lucynda
Pham,a Zhijie Liang,a,c Jun
Wang,a Yi Xu,a Reuben
Bettinger,a John Zientko,a Aaron
P. Esser-Kahnb and Wenjun
Dua*
Page No. – Page No.
From glucose to polymers---
A continuous enzymatic
process process
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