Enzyme-catalyzed synthesis of natural and unnatural polysaccharides

Synthesis of natural and unnatural polysaccharide was achieved via “enzymatic polymerization” by utilizing a glycoside hydrolase as catalyst. Particularly, hyaluronan, chondroitin, and their derivatives belonging to glycosaminoglycans have been prepared using sugar oxazoline monomers designed on the basis of the concept “transition-state analogue substrate”. The oxazoline derivatives of N-acetylhyalobiuronate [GlcAβ(1→3)GlcNAc] and N-acetylchondrosine [GlcAβ(1→3)GalNAc], which have the repeating disaccharide structures of hyaluronan and chondroitin, respectively, were successfully polymerized by the catalysis of hyaluronidase, giving rise to synthetic hyaluronan and chondroitin. Their 2-substituted oxazoline derivatives were also polymerized to the corresponding N-acylated hyaluronan and chondroitin derivatives. Furthermore, N-acetylchondrosine oxazoline derivatives sulfated at the C4, the C6, and both the C4 and C6 of the GalNAc unit were catalyzed by hyaluronidase; the monomer sulfated at the C4 was polymerized to chondroitin 4-sulfate with well-defined structure, whereas the other two monomers were exclusively hydrolyzed to the corresponding disaccharides. These different kinds of natural and unnatural polysaccharides having relatively high molecular weights were produced in all cases by the catalysis of hyaluronidase. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 5014–5027, 2006     

Concentration effects in the cationic ring‐opening polymerization of 2‐ethyl‐2‐oxazoline in N,N‐dimethylacetamide

The monomer concentration for the cationic ring‐opening polymerization of 2‐ethyl‐2‐oxazoline in N,N‐dimethylacetamide was optimized utilizing high‐throughput experimentation methods. Detailed ¹H‐NMR spectroscopic investigations were performed to understand the mechanistic aspects of the observed concentration effects. Finally, the improved polymerization concentration was applied for the synthesis of higher molecular weight (> 10,000 Da) poly(2‐ethyl‐2‐oxazoline)s. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 1487–1497, 2005     

Toward the design of LPEI containing block copolymers: Improved synthesis protocol,selective hydrolysis,and detailed characterization

The synthesis of poly(2‐ethyl‐2‐oxazoline)‐b‐linear poly(ethylenimine) (PEtOx‐b‐LPEI) copolymers by selective basic hydrolysis of PEtOx‐b‐poly(2‐H‐2‐oxazoline) (PEtOx‐b‐PHOx) is described. For this purpose, an easy method for the preparation of the 2‐H‐2‐oxazoline (HOx) monomer was developed. Based on the microwave‐assisted polymerization kinetics for this monomer, PEtOx‐b‐PHOx copolymers were prepared. Subsequently, the block copolymers were selectively hydrolyzed to PEtOx‐b‐LPEI under basic conditions. The success of the polymerizations and subsequent post‐polymerization reactions was demonstrated by ¹H NMR spectroscopy and MALDI‐TOF‐MS investigations of the obtained polymers. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012     

The role of excess nitroxide in the SG1 (N-tert-butyl-N-[1-diethylphosphono-(2,2-dimethylpropyl)] nitroxide)-mediated polymerization of methyl methacrylate

Methyl methacrylate (MMA) polymerizations have been conducted in the presence of large excesses of N-tert-butyl-N-[1-diethylphosphono-(2,2-dimethylpropyl) nitroxide] (SG1) at 110°C. It is demonstrated that such a protocol does not improve control/livingness in the nitroxide mediated polymerization (NMP) of this monomer, instead substantial levels of disproportionation between the nitroxide and propagating radical (PMMA^•) results. The extent of the disproportionation reaction increased with the SG1 concentration, eventually becoming the sole end forming event. Significant disproportionation between SG1 and PMMA^• was also observed at substantially lower temperatures (45°C) in the presence of large excesses of SG1. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 2194–2203, 2007     

Novel N‐methylbenzothiazolium salts as hardeners for epoxy and acrylate monomers

Novel N‐methylbenzothiazolium salts [N‐methyl‐2‐benzylthiobenzothiazolium, N‐methyl‐2‐(4‐nitrobenzylthio)benzothiazolium, N‐methyl‐2‐(1‐ethoxycarbonylethylthio)benzothiazolium, and N‐methyl‐2‐methylthiobenzothiazolium hexafluoroantimonates] were synthesized by the reaction of the corresponding 2‐substituted benzothiazole with dimethylsulfate, followed by anion exchange with KSbF₆. These benzothiazolium salts cationically polymerized an epoxy monomer by photoirradiation. They also polymerized an acrylate monomer via a photoradical process. The use of aromatic compounds such as 2‐ethyl‐9,10‐dimethoxyanthracene as photosensitizers was effective in enhancing the polymerization. These benzothiazolium salts also served as thermal cationic initiators. © 2003 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 41: 3828–3837, 2003     

Detailed study of the ring-opening metathesis polymerization of norbornene bearing a five- or six-membered ring cyclic carbonate along with volume expansion

The ring-opening metathesis polymerization (ROMP) of norbornene derivatives bearing five- or six-membered cyclic carbonate ( 2 or 3 ) was carried out with a typical ruthenium catalyst [bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride], the so-called first-generation Grubbs catalyst, under various reaction conditions, to smoothly obtain the corresponding polyalkenamers ( 5 and 6 ) along with volume expansion. The number-average molecular weights (M_n's), 10% weight loss decomposition temperatures, glass-transition temperatures (T_g's), and volume expansion ratios of the resulting products depended on the polymerization conditions. The degree of volume expansion was mainly affected by M_n, T_g, and the cis/trans configuration of the exocyclic double bonds of the resulting polymers. The volume expansion was confirmed to specifically occur during the polymerization of the monomer bearing cyclic carbonate moieties, and similar ROMPs of monomers without cyclic carbonate, such as norbornene itself, the monomer 5,5-bis(methoxymethyl)bicyclo[2.2.1]hept-2-ene, and the monomer endo-N-methylbicyclo[2.2.1]hept-5-ene-2,3-dicarboxylimide, proceeded along with volume shrinkage. Furthermore, an investigation of another type of polymerization, a vinyl-type one, of monomer 2 suggested that the volume expansion specifically took place in the ring-opening type of polymerization. In addition, the Sc(OTf)₃-mediated cationic ring-opening reaction of the cyclic carbonate moiety of polyalkenamer 5 smoothly proceeded along with volume expansion or nearly zero volume shrinkage to yield the corresponding networked polymer. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 395–405, 2006     

Synthesis of a new 2‐amino‐glycan,poly‐(1→6)‐α‐D‐mannosamine,by ring‐opening polymerization of 1,6‐anhydro‐mannosamine derivatives

A stereoregular 2‐amino‐glycan composed of a mannosamine residue was prepared by ring‐opening polymerization of anhydro sugars. Two different monomers, 1,6‐anhydro‐2‐azido‐mannose derivative ( 3 ) and 1,6‐anhydro‐2‐(N, N‐dibenzylamino)‐mannose derivative ( 6 ), were synthesized and polymerized. Although 3 gave merely oligomers, 6 was promptly polymerized into high polymers of the number‐average molecular weight (M_n) of 2.3 × 10⁴ to 2.9 × 10⁴ with 1,6‐α stereoregularity. The differences of polymerizability of 3 and 6 from those of the corresponding glucose homologs were discussed. It was found that an N‐benzyl group is exceedingly suitable for protecting an amino group in the polymerization of anhydro sugars of a mannosamine type. The simultaneous removal of O‐ and N‐benzyl groups of the resulting polymers was achieved by using sodium in liquid ammonia to produce the first 2‐amino‐glycan, poly‐(1→6)‐α‐D ‐mannosamine, having high molecular weight through ring‐opening polymerization of anhydro sugars.© 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012     

Poly[(4-N-ethylene-N-ethylamino)-α-cyanocinnamate]: A nonlinear optical polymer with a chromophoric mainchain. I. Synthesis and spectral characterization

Poly[(4-N-ethylene-N-ethylamino)-α-cyanocinnamate] was prepared by solution esterification of (4-N-ethyl-N-(2-hydroxyethyl) amino)-α-Cyanocinnamic acid and by melt transesterification of ethyl (4-N-ethyl-N-(2-hydroxyethyl) amino)-α-cyanocinnamate. The melt transesterification generally yielded polymer with a number-average molecular weight of about 10,200 by gel permeation chromatography (GPC) versus polystyrene standards. The polymer was found to be amorphous with a glass transition temperature of about 103°C by differential scanning calorimetry (DSC). The solution esterification generally gave a polymer with a number-average molecular weight of about 2200 by GPC versus polystyrene standards. This polymer was found to have a glass transition temperature varying between 60 and 90°C by DSC. The infrared (IR) spectrum of the polymer made from both methods were analyzed in detail. The ¹H- and ¹³C-NMR spectra of the meltsynthesized ethyl cinnamate derivative polymer are consistent with the reported structure.     

Metallocene‐mediated cationic ring‐opening polymerization of 2‐methyl‐ and 2‐phenyl‐oxazoline

The cationic ring‐opening polymerization of 2‐methyl‐2‐oxazoline and 2‐phenyl‐2‐oxazoline was efficiently used using bis(η⁵‐cyclopentadienyl)dimethyl zirconium, Cp₂ZrMe₂, or bis(η⁵‐tert‐butyl‐cyclopentadienyl)dimethyl hafnium in combination with either tris(pentafluorophenyl)borate or tetrakis(pentafluorophenyl)borate dimethylanilinum salt as initiation systems. The evolution of polymer yield, molecular weight, and molecular weight distribution with time was examined. In addition, the influence of the initiation system and the monomer on the control of the polymerization was studied. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 000: 000–000, 2011     

A Colorimetric Assay to Enable High-Throughput Identification of Biofilm Exopolysaccharide-Hydrolyzing Enzymes

Glycosidase enzymes that hydrolyze the biofilm exopolysaccharide poly-β-(1→6)-N-acetylglucosamine (PNAG) are critical tools to study biofilm and potential therapeutic biofilm dispersal agents. Function-driven metagenomic screening is a powerful approach for the discovery of new glycosidase but requires sensitive assays capable of distinguishing between the desired enzyme and functionally related enzymes. Herein, we report the synthesis of a colorimetric PNAG disaccharide analogue whose hydrolysis by PNAG glycosidases results in production of para-nitroaniline that can be continuously monitored at 410 nm. The assay is specific for enzymes capable of hydrolyzing PNAG and not related β-hexosaminidase enzymes with alternative glycosidic linkage specificities. This analogue enabled development of a continuous colorimetric assay for detection of PNAG hydrolyzing enzyme activity in crude E. coli cell lysates and suggests that this disaccharide probe will be critical for establishing the functional screening of metagenomic DNA libraries.     

Chemo-enzymatic Synthesis of Novel Oligo-N-acetyllactosamine Derivatives having a β(1-4)–β(1-6) Repeating Unit by Using Transition State Analogue Substrate

Chitinase-catalyzed hydrolytic and transglycosylating behavior of 1,2-oxazoline derivative of N-acetyllactosamine (LacNAc-oxa) 1 has been investigated. An extremely rapid hydrolysis (ring-opening of the oxazoline moiety) could be observed, suggesting that 1 behaves as a transition state analogue substrate for chitinase A1 (Bacillus circulans WL-12). This disaccharide monomer 1 was found to polymerize under basic conditions, giving rise to novel oligosaccharides having a β(1-4)–β(1-6) repeating unit in the main chain. The degree of polymerization of the resulting oligosaccharides was up to 5. This is the first example of enzymatic glycosylation reaction forming a β(1-6) bond catalyzed by chitinase.     

Desoxy-nitrozucker. 13. Mitteilung. Herstellung ungeschützter und partiell geschützter 1-Desoxy-1-nitro-D-aldosen sowie Röntgenstrukturanalysen einiger ihrer Vertreter

Preparation of Unprotected and Partially Protected 1-Deoxy-1-nitro-D -aldoses and Some Representative X-Ray Structure Analyses The unprotected and partially protected 1-deoxy-1-nitro derivatives of α-and β-D -glucopyranose (see 15 and 14 ), β-D -mannopyranose (see 16 ), N-acetyl-β-D -glucosamine (see 17 ), β-D -galactofuranose (see 19 ), β-D -ribofuranose (see 20 ), α-D -arabinofuranose (see 21 ), 4,6-O-benzylidene-β-D -glucose (see 40 ), N-acetyl-4,6-O-benzylidene-β-D -glucosamine (see 41 ), and 4,6-O-benzylidene-β-D -galactose (see 42 ) were prepared by ozonolysis of the corresponding nitrones which were obtained from the acid-catalyzed reaction of p-nitrobenzaldehyde with the hydroxylamine 4 , the unprotected oximes 3 and 5–9 and the 4,6-O-benzylidene oximes 35–37 , respectively (Schemes 1–3). The gluco- and manno-nitrones 10 and 12 were isolated, and their ring size and their anomeric and (E/Z) configurations were determined by NMR spectroscopy and by their transformation into their corresponding nitro derivatives. The structure of the deoxynitroaldoses were determined by NMR spectroscopy, polarimetry, and, in the case of 14 , 16 , and 17 , by formation of the 4,6-O-benzylidene ( 14 → 40 ) or 4,6-O-isopropylidene ( 16 → 43 , 17 → 23 ) derivatives (Scheme 3). Acetylation of the nitroglucopyranose 14 , the 2-acetamido-nitroglucopyranose 17 , and the nitrogalactofuranose 19 gave the crystalline peracetylated nitroaldoses 22 , 24 , and 45 , respectively (Scheme 4, Figs. 1 and 3); acetylation of the nitromannopyranose 16 gave the nitro-arabino-glycal 44 (Scheme 4). The structure of the peracetylated nitroglucopyranose 22 , the nitroglucosamine 25 , the nitrogalactofuranose 45 , and the nitroribofuranose 20 were confirmed by X-ray analysis (Figs. 1 4). In all cases, including the β-D -glucopyranose derivative 22 , considerably shortening of the (endocyclic) C(1)-O bond was observed. Base-catalyzed anomerization of the β-D -configurated nitroglucopyranose 14 , the nitromannopyranose 16 , the benzylidene acetal 40 of nitroglucose, and the 2,3,4,6-tetraacetylated glucosamine derivative 24 gave the corresponding nitro-α-D -aldoses 15 , 26 , 47 , and 25 , respectively (Scheme 4).     

Synthesis of [D-alanine, 4'-azido-3',5'-ditritio-L-phenylalanine, norvaline4[alpha-melanotropin as a 'photoaffinity probe' for hormone-receptor interactions (author's transl)]

Synthesis of [D -alanine¹, 4′-azido-3′, 5′-ditritio-L -phenylalanine², norvaline⁴]α-melanotropin as a ‘photoaffinity probe’ for hormone-receptor interactions. The synthesis of an α-MSH derivative containing 4′-azido-3′,5′-ditritio-L -phenylalanine is described: Ac · D -Ala-Pap(³H₂)-Ser-Nva-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val · NH₂. This hormone analogue is being used for specific photoaffinity labelling of receptor molecules. The synthesis was performed in a way to minimize the number of radioactive steps and to introduce the radio-active and the photoaffinity label exclusively into position 2. The dipeptide N(α)-acetyl-D -alanyl- (4′-amino-3′,5′-diiodo)-L -phenylalanine was tritriated and transformed into the azido compound, N(α)-acetyl-D -alanyl-(4′-azido-3′,5′-ditritio)-L -phenylalanine which was then condensed with H · Ser-Nva-Glu(OtBu)-His-Phe-Arg-Trp-Gly-Lys(BOC)-Pro-Val · NH₂ to the tridecapeptide. The α-MSH analog displayed a specific activity of 11 Ci/mmol, and a biological activity of about 4 · 10⁹ U/mmol (10% of α-MSH).     

Synthesis of New Nucleosides by coupling of chloropurines with 2- and 3-deoxy derivatives of N-methyl-D-ribofuranuronamide

The synthesis of new deoxyribose nucleosides by coupling chloropurines with modified D -ribose derivatives is reported. The methyl 2-deoxy-N-methyl-3-O-(p-toluoyl)-α-D -ribofuranosiduronamide (α-D - 8 ) and the corresponding anomer β-D - 8 were synthesized starting from the commercially available 2-deoxy-D -ribose ( 1 ) (Scheme 1). Reaction of α-D - 8 with the silylated derivative of 2,6-dichloro-9H-purine ( 9 ) afforded regioselectively the N⁹-(2′-deoxyribonucleoside) 10 as anomeric mixture (Scheme 2), whereas β-D - 8 did not react. Glycosylation of 9 or of 6-chloro-9H-purine ( 17 ) with 1,2-di-O-acetyl-3-deoxy-N-methyl-β-D -ribofuranuronamide ( 13 ) yielded only the protected β-D -anomers 14 and 18 , respectively (Scheme 3). Subsequent deacetylation and dechlorination afforded the desired nucleosides β-D - 11 , β-D - 12,15 , and 16 . The 3′-deoxy-2-chloroadenosine derivative 15 showed the highest affinity and selectivity for adenotin binding site vs. A₁ and A_2A adenosine receptor subtypes.     

Amphiphilic gradient copolymers containing fluorinated 2‐phenyl‐2‐oxazolines: Microwave‐assisted one‐pot synthesis and self‐assembly in water

Here, we present the one‐step synthesis of 2‐(m‐difluorophenyl)‐2‐oxazoline and its use as a monomer for microwave‐assisted statistical cationic ring‐opening copolymerizations (CROP). Well‐defined amphiphilic gradient copolymers, as evidenced by the polymerization kinetics, were prepared using 2‐ethyl‐2‐oxazoline as comonomer and methyl tosylate as initiator in nitromethane at 140 °C. The resulting gradient copolymers (DP = 60 and 100) were characterized by means of size exclusion chromatography and ¹H NMR spectroscopy. In the second part, we focus on a detailed study of the self‐assembly of the copolymers in aqueous solution using atomic force microscopy and dynamic light scattering. Both methods revealed the self‐assembly of the gradient copolymers into spherical micelles. To quantify the influence of the fluorine atoms and the monomer distribution on the self‐assembly, a comparative study with gradient copolymers of 2‐phenyl‐2‐oxazoline and 2‐ethyl‐2‐oxazoline was performed. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 5859–5868, 2008     

Synthesis and polymerization of 5‐(methacrylamido)tetrazole,a water‐soluble acidic monomer

The reaction of methacryloyl chloride with 5‐aminotetrazole gave the polymerizable methacrylamide derivative 5‐(methacrylamido)tetrazole ( 4 ) in one step. The monomer had an acidic tetrazole group with a pK_a value of 4.50 ± 0.01 in water methanol (2:1). Radical polymerization proceeded smoothly in dimethyl formamide or, after the conversion of monomer 4 into sodium salt 4‐Na , even in water. A superabsorbent polymer gel was obtained by the copolymerization of 4‐Na and 0.08 mol % N,N′‐methylenebisacrylamide. Its water absorbency was about 200 g of water/g of polymer, although the extractable sol content of the gel turned out to be high. The consumption of 4‐Na and acrylamide (as a model compound for the crosslinker) during a radical polymerization at 57 °C in D₂O was followed by ¹H NMR spectroscopy. Fitting the changes in the monomer concentration to the integrated form of the copolymerization equation gave the reactivity ratios r _4‐Na = 1.10 ± 0.05 and r_acrylamide = 0.45 ± 0.02, which did not differ much from those of an ideal copolymerization. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 40: 4333–4343, 2002     

One‐pot synthesis of 2‐phenyl‐2‐oxazoline‐containing quasi‐diblock copoly(2‐oxazoline)s under microwave irradiation

The microwave‐assisted statistical copolymerization of 2‐phenyl‐2‐oxazoline with 2‐methyl‐2‐oxazoline or 2‐ethyl‐2‐oxazoline is discussed in this contribution. Kinetic studies of these statistical copolymerizations as well as reactivity ratio determinations were performed to investigate the monomer distribution in these copoly(2‐oxazoline)s, demonstrating the formation of quasi‐diblock copolymers. In addition, the synthesis of copolymer series with monomer concentrations ranging from 0 to 100 mol % is described. These copolymer series were characterized with ¹H NMR spectroscopy, gas chromatography, and gel permeation chromatography. Moreover, the glass‐transition temperatures and solubility of these copolymers were studied, and this revealing better mixing of poly(2‐methyl‐2‐oxazoline) (pMeOx) with poly(2‐phenyl‐2‐oxazoline) (pPhOx) than poly(2‐ethyl‐2‐oxazoline) (pEtOx) with poly(2‐phenyl‐2‐oxazoline) (pPhOx). © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 416–422, 2007.     

SYNTHESIS AND CATIONIC RING-OPENING POLYMERIZATION OF 1, 4-ANHYDRO-2, 3-DI-O-(P-AZIDOBENZYL)-α-D-RIBOPYRANOSE

New highly stereoregular 2, 3 -di- O-(p-azidobenzyl )-(1 →5 ) - α-D -ribofuranan was synthesized byselective ring-opening polymerization of 1, 4-anhydro-2, 3 - di-O -(p-azidobenzyl )-α-D -ribopyranose(ADABR) using phosphorus pentafluoride or tin tetrachloride as catalyst at low temperature indichloromethane. The monomer was obtained by the reaction of p - bromomethyl -phenyleneazide with 1, 4 -anhydro-α-D-ribose in DMF. The structure of poly(ADANR) was identified by specific rotation and ~(13)C-NMR spectroscopy. Acid chloride-AgCl_4 complex catalyst such as CH_2=C(CH_3)C~+OClO_4~- used in thepolymerization resulted in polymers with mixed structures, i.e. (1→5)-α-D-ribofuranosidic and (1→4)-β-D-ribopyranosidic units. However, with C_6H_5C~+OClO_4~- as catalyst, pure (1→5)-α-D-ribofuranan was obtained.The effects of catalyst, polymerization temperature and time on polymer stereoregularity were examined, andthe mechanism of the ring-opening polymerization was discussed.     

Synthesis of polymers by template polymerization. I. Template polymerization of poly(methacrylic acid) with β‐cyclodextrin

A novel template monomer with multiple methacryloyl groups was synthesized with β‐cyclodextrin by the acetylation of primary hydroxyl groups and the esterification of secondary hydroxyl groups with methacrylic acid anhydride. The average number of methacryloyl groups in the monomer was 11. The radical polymerization of the monomer was carried out with the following initiators: α,α′‐azobisisobutylonitrile, H₂O₂? Fe²⁺ redox initiator, p‐xylyl‐N,N‐dimethyldithiocarbamate (XDC), and α‐bromo‐p‐xylyl‐N,N‐dimethyldithiocarbamate (BXDC). When the concentration of the monomer was less than 4.12 × 10^?3 M, polymerization was limited inside the molecule, and gelation of the system was hindered. For controlled radical photopolymerization with XDC and BXDC, the methacryloyl groups of the monomer were homogeneously polymerized, and poly(methacrylic acid) with a narrow molecular weight distribution was obtained by the hydrolysis of the polymerized products. © 2001 John Wiley & Sons, Inc. J Polym Sci Part A: Polym Chem 39: 3539–3546, 2001     

Synthesis and ring‐opening polymerizations of novel S‐glycooxazolines

A new 2‐oxazolines containing S‐galactosyl substituents linked to alkyl chains of different lengths; (S‐glycooxazoline) were prepared relatively in high yields. By using a 1:1 adduct of 2‐methyl‐2‐oxazoline and methyl triflate, as the initiator, the monomer was polymerized via ring‐opening polymerization (ROP) to give products with relatively narrow molecular weight distributions. Homo‐ and copolymerization were performed, and the kinetics of these new S‐glycooxazolines in the ROP are investigated. After a quantitative deprotection, poly(2‐oxazoline)s having pendant carbohydrate were obtained. The interaction of the poly(S‐glycooxazoline) with RCA₁₂₀ lectin was investigated, the binding constant between glycopolymer and lectin was increased by 10² times compared with that of the monosaccharide (D ‐galactose). The in vivo expression of green fluorescent protein using the synthesized poly(S‐glycooxazoline)s as polymeric inducers in Escherichia coli host were performed. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010