In vitro synthesis of cellulose and related polysaccharides

Progress in Polymer Science (Oxford)

Volumn 26, Issue 9, 2001, Pages 1525-1560

  Kobayashi, Shiro ^a   Sakamoto, Junji ^a   Kimura, Shunsaku ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Cellulase; Cellulose; Chitin; Chitinase; Enzymatic polymerization; Glycosylase; In vitro synthesis; Polysaccharide; Xylan

Indexed keywords

CATALYSTS; CHITIN; ENZYMES; HYDROLYSIS; MONOMERS; POLYMERIZATION; SYNTHESIS (CHEMICAL); XYLENE;

ENZYMATIC POLYMERIZATION;

CELLULOSE;

CELLULASE;

EID: 0035506045     PISSN: 00796700     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0079-6700(01)00026-0     Document Type: Review

References (170)

1. Fifty years of cellulose research
2. New approaches to advanced polymers by selective cellulose functionalization
3. New ionic polymers by cellulose functionalization
4. Formation and properties of the lyotropic mesophase of the cellulose mixed inorganic acid system
5. Membranes from polyelectrolyte complexes
6. Size exclusion redox-labeled immunoassay (SERI): A new format for homogeneous amperometric creatinine determination
7. Suitability of cellulose molecular dialysis membrane for bioartificial pancreas: In vitro biocompatibility studies
8. Ultrathin films of cellulose on silicon-wafers
9. The Koenigs-Knorr reaction
10. Simple syntheses of α- and β-O-glycosyl imidates; Preparation of glycosides and disaccharides
11. A new stereoselective synthesis of methyl 1,2-trans-1-thio-glycosides
12. Glycosylation using a thioglycoside and methyl trifluoromethanesulfonate - A new and efficient method for cis and trans glycoside formation
13. Practical synthesis of oligosaccharides - Partial synthesis of avermectin-B1A
14. An efficient method for glucosylation of hydroxy compounds using glucopyranosyl fluoride
15. Normal-pentenyl esters versus normal-pentenyl glycosides - Synthesis and reactivity in glycosidation reactions
16. Trityl tetrakis(pentafluorophenyl)borate catalyzed stereoselective glycosylation using glycopyranosyl fluoride as a glycosyl donor
17. Recent advances in the chemoenzymatic synthesis of carbohydrates and carbohydrate mimetics
18. Advances in selective chemical syntheses of complex oligosaccharides
19. Recent progress in O-glycosylation methods and its application to natural-products synthesis
20. Experiments directed towards glycoconjugate synthesis
21. Glycosylation reactions - Present status future directions
22. Strategies and tactics in oligosaccharide synthesis
23. Recent developments in oligosaccharide synthesis
24. Enzymatic polymerization and oligomerization
25. Enzymatic catalysis
26. Enzymatic polymerization: A new method of polymer synthesis
27. Enzymatic polymerization for precision polymer synthesis
28. Enzymes in polymer science: An introduction
29. In vitro enzymic synthesis of polymers containing saccharides, lignins, proteins or related compounds: A review
30. Enzymatic polymerization
31. Enzymes as catalysts in synthetic organic chemistry
32. Enzymatic polymerization - Synthesis of artificial polymers catalyzed by natural polymers
33. Glycosylation employing bio-systems: From enzymes to whole cells
34. Enzyme-catalyzed oligosaccharide synthesis
35. A fresh understanding of the stereochemical behavior of glycosylases: Structural distinction of inverting (2-MCO-type) versus retaining (1-MCO-type) enzymes
36. Synthesis and modification of carbohydrates using glycosidases and lipases
37. Configurational specificity: Unappreciated key to understanding enzymic reversions and de novo glycosidic bond synthesis
38. Enzymatic transformations in supersaturated substrate solutions: I. A general study with glycosidases
39. Optimization of the enzymatic synthesis of butyl glucoside using response surface
40. Enzymatic synthesis and modification of polymers in nonaqueous solvents
41. Reverse hydrolysis catalysed by β-N-acetylhexosaminidase from Aspergillus oryzae
42. Enzymic synthesis of useful chito-oligosaccharides utilizing transglycosylation by chitinolytic enzymes in a buffer containing ammonium sulfate
43. Regioselective synthesis of useful oligosaccharides by glycosidase
44. Glycosyl fluorides in enzymatic reactions
45. The hydrolysis of glycosyl fluorides by glycosidases
46. Glycanase-catalyzed synthesis of non-natural oligosaccharides
47. Novel method for polysaccharide synthesis using an enzyme: The first in vitro synthesis of cellulose via a nonbiosynthetic path utilizing cellulase as catalyst
48. Enzymatic polymerization - The 1st in vitro synthesis of cellulose via nonbiosynthetic path catalyzed by cellulase
49. Packing analysis of carbohydrates and polysaccharides III. Valonia cellulose and cellulose II
50. Structure of native cellulose
51. Crystal morphology, biosynthesis, and physical assembbly of cellulose, chitin, and chitosan
52. Morphology of native cellulose related to the biological synthesis
53. Assembly of synthetic cellulose I
54. Direct visualization of synthetic cellulose formation via enzymatic polymerization using transmission electron microscopy
55. β-glucan synthesis in the cotton fiber. IV. In vitro assembly of the cellulose I allomorph
56. Chemical synthesis of native-type cellulose and its analogues via enzymatic polymerization
57. Formation and structure of artificial cellulose spherulites via enzymatic polymerization
58. Structure of spherulites of bacterial cellose from acetobacter-XYLINUM
59. Cellulase-catalysed glycosylation reactions: Simple route towards a highly selective synthesis of oligosaccharides
60. A novel method for synthesis of cellooligosaccharide derivatives by using enzyme catalyst
61. The predominantly nonhydrolytic action of α-amylases on α-maltosyl fluoride
62. How α- and β-amylases achieve their perfect stereoselectivity
63. Enzymatic polymerization of α-d-maltosyl fluoride utilizing α-amylase as the catalyst: A new approach for the synthesis of maltooligosaccharides
64. Specific preparation of artificial xylan: A new approach to polysaccharide synthesis by using cellulase as catalyst
65. Synthesis of artificial chitin: Irreversible catalytic behavior of a glycosyl hydrolase through a transition state analogue substrate
66. Ethylenimine polymers
67. Hydrolysis and polymerization of novel monomers containing amino suger
68. Synthesis of artificial chitin by enzymatic ring-opening polyaddition
69. Artificial chitin spherulites composed of single crystalline ribbons of α-chitin via enzymatic polymerization
70. Liquid crystal systems from fibrillar polysaccharides
71. Scarabaeid beetle exocuticle as an optical analogue of cholesteric liquid crystals
72. Synthesis of 6- and/or 6′-O-methylated cellobiosyl fluorides: New monomers for enzymatic polymerization
73. Synthesis of alternatingly 6-O-methylated cellulose via enzymatic polymerization of a substituted cellobiosyl fluoride monomer catalyzed by cellulase
74. Xylanase-catalyzed synthesis of a novel polysaccharide having a glucose-xylose repeating unit, a cellulose-xylan hybrid polymer
75. Thiooligosaccharides in glycobiology
76. Enzymic synthesis of hemithiocellodextrins
77. Transglycosylation activity of Bacillus 1,3-1,4-β-d-glucan 4-glucanohydrolases. Enzymic synthesis of alternate 1,3-1,4-β-d-glucooligosaccharides
78. Mechanism of lysozyme action
79. Active site of lysozyme - Some properties of subsites E and F
80. Substrate-assisted catalysis unifies two families of chitinolytic enzymes
81. Substrate assistance in the mechanism of family 18 chitinases: Theoretical studies of potential intermediates and inhibitors
82. Stereochemistry of chitin hydrolysis by a plant chitinase/lysozyme and X-ray structure of a complex with allosamidin: Evidence for substrate assisted catalysis
83. Substrate distortion to a boat conformation at subsite -1 is critical in the mechanism of family 18 chitinases
84. Three-dimensional structure of the catalytic domain of chitinase A1 from Bacillus circulans WL-12 at a very high resolution
85. The role of enzyme distortion in the single displacement mechanism of family 19 chitinases
86. Stereochemistry and the mechanism of enzymatic reactions
87. Mutagenesis of glycosidases
88. Glycosidase mechanism: Anatomy of a finely tuned catalyst
89. Catalytic reaction mechanism on α-secondary kinetic isotope effects in hydrolytic cleavage of α-glucosidic linkage by α-glycosidases
90. Trapping and characterization of the reaction intermediate in cyclodextrin glycosyltransferase by use of activated substrates and a mutant enzyme
91. How amylases achieve their perfect stereoselectivity
92. Changing enzymatic-reaction mechanisms by mutagenesis - Conversion of a retaining glucosidase to an inverting enzyme
93. Mechanisms of enzymic glycoside hydrolysis
94. Structures and mechanisms of glycosyl hydrolases
95. Studies of the cellulolytic system of the filamentous fungus Trichoderma reesei QM 9414. Substrate specificity and transfer activity of endoglucanase I
96. Stereochemistry, specificity and kinetics of the hydrolysis of reduced cellodextrins by nine cellulases
97. The concept of the α-amylase family: Structural similarity and common catalytic mechanism
98. The α-amylases as glycosylases, with wider catalytic capacities than envisioned or explained by their representation as hydrolases
99. Comparison of action of cyclodextrin glucanotransferase from Bacillus megaterium, B. circulans, B. stearothermophilus and B. macerans
100. Pattern of action of Bacillus stearothermophilus neopullulanase on pullulan
101. Action of neopullulanase: Neopullulanase catalyzes both hydrolysis and translgycosylation at α-1,4- and α-1,6-glucosidic linkages
102. Analysis of active center of Bacillus stearothermophilus neopullulanase
103. Glycosidases - A great synthetic tool
104. Synthesis of the disaccharide 6-O-β-d-galactopyranosyl-2-acetamido-2-deoxy-d-galactose using immobilized β-galactosidase
105. Regioselective synthesis of p-nitrophenyl glycosides of β-d-galactopyranosyl-disaccharides by transglycosylation with β-d-galactosidases
106. Two decades of research on biosynthesis of saccharides
107. Cellulose biosynthesis in higher plants
108. Cellulose biosynthesis: Exciting times for a difficult field of study
109. Cellulose and callose biosynthesis in higher plants I. Solubilization and separation of (1 → 3)- and (1 → 4)-β-glucan synthase activities from mung bean
110. β-glucan synthesis in the cotton fiber
111. β-glucan synthesis in the cotton fiber-Glucan synthesis in the cotton fiber I. Identification of β-1,4- and β-1,3-glucans synthesized in vitro
112. β-glucan synthesis in the cotton fiber IV. In vitro assembly of the cellulose I allomorph
113. Recent progress in the field of cellulose synthesis
114. Tubulin-containing granules in the plasma membranes of azuki bean epicotyls and their relationship to the synthesis of β-glucan
115. Multidomain architecture of β-glycosyl transferases: Implications for mechanism of action
116. Glycogen synthase and glycogen synthase kinases
117. The mechanism of glycogen synthetase as determined by deuterium isotope effects and positional isotope exchange experiments
118. Glycosyl fluorides can function as substrates for nucleotide phosphosugar-dependent glycosyltransferases
119. High-efficient synthesis of sialyloligosaccharides and sialoglycopeptides
120. Enzymes in organic synthesis: Application to the problems of carbohydrate recognition (Part 2)
121. Enzymatic synthesis of hyaluronic acid with regeneration of sugar nucleotides
122. Functional domains in the chitin oligosaccharide synthase NodC and related β-polysaccharide synthases
123. Donor substrate specificity of recombinant human blood groups A, B and hybrid A/B glycosyltransferases expressed in escherichia coli
124. Living-polymerization und enzymatische polysaccaridsynthese
125. Phosphorolytic syntheses with di-, oligo- and multi-functions primers
126. Enzymatic grafting of amylose from poly(dimethylsiloxanes)
127. The enzymatic-synthesis and NMR characterization of specifically deoxygenated and fluorinated glycogens
128. Synthesis of 2-deoxy-β-d-arabino-hexopyranosyl phosphate and 2-deoxy-maltooligosaccharides with phosphorylase
129. Phosphorolytic synthesis of cellodextrins
130. Crystal structures of the cellulase Cel48F in complex with inhibitors and substrates give insights into its processive action
131. Site-directed mutation of moncatalytic residues of Thermobifida fusca exocellulase Cel6B
132. Tryptophan 272: An essentail determinant of crystalline cellulose degradation by trichoderma reesei cellobiohydrolase Cel6A
133. High-resolution crystal structures reveal how a cellulose chain is bound in the 50 Å long tunnel of cellobiohydrolase I from Trichoderma reesei
134. Phosphorylase recognition and phosphorolysis of its oligosaccharide substrate: Answers to a long outstanding question
135. Glycosynthases: Mutant glycosidases for oligosaccharide synthesis
136. Understanding and exploiting glycosidases
137. The E358S mutant of Agrobacterium sp. β-glucosidase is a greatly improved glycosynthase
138. From β-glucanase to β-glucansynthase: Glycosyl transfer to β-glycosyl fluorides catalyzed by a mutant endoglucanase lacking its catalytic nucleophile
139. Highly efficient synthesis of β - (1 → 4)-oligo and polysaccharides using a mutant cellulase
140. Structure-based design of a lysozyme with altered catalytic activity
141. Structural basis of the conversion of T4 lysozyme into a transglycosidase by reengineering the active site
142. Synthesis of unbranched polysaccharides
143. Synthesis of polysaccharides with a regular structure
144. Synthesis of polysaccharides. 17. Synthesis of α-1,4-mannan
145. Synthesis of homo- and heteropolyuronide derivatives
146. Synthesis of polysaccharides. 10. Synthesis of regular glucan with alternating α - 1 → 4- and β - 1 → bonds
147. Synthesis and polymerization of anhydro sugars
148. Chemical synthesis of a stereoregular linear polysaccharide
149. Artificial polysaccharides and their biological activities
150. Selective ring-opening polymerization of 1,4-anhydro-α-d-ribopyranose derivatives and synthesis of stereoregular (1,4)-β-d-ribopyranan
151. Selective ring-opening polymerization of di-O-methylated and di-O-benzylated 1,4-anhydro-β-d-ribopyranoses and structure proof of synthetic cellulose-type polysaccharide (1,4)-β-d-ribopyranan and (1,5)-β-d-ribofuranan
152. Synthesis of a novel cellulose-type hexopyranan 6-deoxy-(1 → 4)-α-l-talopyranan by selective ring-opening polymerization of 1,4-anhydro sugar derivatives
153. Seletive synthesis of cellulose-type copolymers by ring-opening copolymerization of 1,4-anhydro-α-d-ribopyranose derivatives
154. Cationic ring-opening polymerization of 3,6-di-O-benzyl-β-d-glucose 1,2,4-orthopivalate and the first chemical synthesis of cellulose
155. Substituent effect on ring-opening polymerization of regioselectively acylated 1,4-anhydro-β-d-glucopyranose derivatives
156. Synthesis of a dibenzylchitin-type polysaccharide by acid-catalyzed polymerization
157. Novel approaches to glycopolymer syntheses from the viewpoint of polymerization chemistry
158. Synthesis of natural- and non-natural-type aminopolysaccharides: 2-acetamido-2-deoxy-β-d-glucopyranan derivatives by acid-catalyzed polymerization of 2-methyl(3,6- and 3,4-di-O-benzyl-1,2-dideoxy-α-d-glucopyrano)-[2,1-d]-2-oxazolines involving stereoregular glycosylation
159. Synthesis of hyperbranched aminopolysaccharides
160. First synthesis of cellooctaose by a convergent synthetic method
161. First stepwise synthesis of cellulose analogs
162. Angiogenesis induced by degradation products of hyaluronic acid
163. Synthesis of a tetrasaccharide fragment of hyaluronic-acid having a glucuronic-acid at the reducing end
164. Synthesis of hyaluronic acid-related di-, tri-, and tetra-saccharides having an N-acetylglucosamine residue at the reducing end
165. Synthetic studies on plant-cell wall glycans. 5. A highly stereocontrolled synthesis of the propyl glycoside of a decagalacturonic acid. A model-compound for the endogenous phytoalexin elicitor-active oligogalacturonic acids
166. Synthetic studies on plant-cell wall glycans. 7. Stereoselective total synthesis of dodecagalcturonic scid, a phytoalexin elicitor of soybean
167. A general and highly efficieent solid phase synthesis of oligosaccharides. Total synthesis of a heptasaccharide phytoalexin elicitor (HPE)
168. Polymer-supported solution synthesis of oligosaccharides
169. Parallel synthesis and screening of a solid phase carbohydrate library