Page 9 of 21
Journal of the American Chemical Society
(16)
Obel, N.; Erben, V.; Schwarz, T.; Kühnel, S.; Fodor, A.;
Esterases of Family CE16 on Artificial and Natural Substrates. J.
Biotechnol. 2016, 233, 228–236.
(34) Guern, J.; Felle, H.; Mathieu, Y.; Kurkdjian, A.
Regulation of Intracellular pH in Plant Cells. Int. Rev. Cytol. 1991,
127, 111–173.
(35) Capek, P.; Alföldi, J.; Lišková, D. An Acetylated
Galactoglucomannan from Picea Abies L. Karst. Carbohydr. Res.
2002, 337, 1033–1037.
Pauly, M. Microanalysis of Plant Cell Wall Polysaccharides. Mol.
Plant 2009, 2, 922–932.
(17)
York, W. S. Effects of the Mur1 Mutation on Xyloglucans
Produced by Suspension-Cultured Arabidopsis Thaliana Cells.
Planta 2001, 214, 67–74.
1
2
3
4
5
6
Pauly, M.; Eberhard, S.; Albersheim, P.; Darvill, A.;
(18)
Petkowicz, C. L. O.; Reicher, F.; Mazeau, K.
7
8
9
Conformational Analysis of Galactomannans: From Oligomeric
Segments to Polymeric Chains. Carbohydr. Polym. 1998, 37, 25–
(36) Woods, R. J.; Pathiaseril, A.; Wormald, M. R.; Edge, C.
J.; Dwek, R. A. The High Degree of Internal Flexibility Observed
for an Oligomannose Oligosaccharide Does Not Alter the
Overall Topology of the Molecule. Eur. J. Biochem. 1998, 258,
372–386.
(37) Hammond, G. S. A Correlation of Reaction Rates. J.
Am. Chem. Soc. 1955, 77, 334–338.
(38) Anslyn, E. V.; Dougherty, D. A. Modern Physical
Organic Chemistry; University Science Books: Sausalito,
Carlifornia, 2006.
(39) Bastardo, L. A.; Mészaros, R.; Varga, I.; Gilányi, T.;
Cleasson, P. M. Deuterium Isotope Effects on the Interaction
between Hyperbranched Polyethylene Imine and an Anionic
Surfactant. J. Phys. Chem. B 2005, 109, 16196–16202.
(40) Mikkelsen, K.; Siguri, A.; Nielsen, O. Acidity
Measurements with the Glass Electrode Is H2O-D2O Mixtures. J.
Phys. Chem. 1952, 458, 1–6.
39.
(19)
Petkowicz, C. L. O.; Reicher, F.; Chanzy, H.; Taravel, F.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
R.; Vuong, R. Linear Mannan in the Endosperm of Schizolobium
Amazonicum. Carbohydr. Polym. 2001, 44, 107–112.
(20) Meier, H.; Reid, J. S. G. Reserve Polysaccharides Other
Than Starch in Higher Plants BT - Plant Carbohydrates I:
Intracellular Carbohydrates; Loewus, F. A., Tanner, W., Eds.;
Springer Berlin Heidelberg: Berlin, Heidelberg, 1982; pp 418–471.
(21)
Huang, X.; Nie, S.; Cai, H.; Zhang, G.; Cui, S. W.; Xie,
M.; Phillips, G. O. Study on Dendrobium Officinale O-Acetyl-
Glucomannan (Dendronan®): Part VI. Protective Effects against
Oxidative Stress in Immunosuppressed Mice. Food Res. Int. 2015,
72, 168–173.
(22) Zhang, G. Y.; Nie, S. P.; Huang, X. J.; Hu, J. L.; Cui, S.
W.; Xie, M. Y.; Phillips, G. O. Study on Dendrobium Officinale O
-Acetyl-Glucomannan (Dendronan®). 7. Improving Effects on
Colonic Health of Mice. J. Agric. Food Chem. 2016, 64, 2485–2491.
(23) Huang, X.; Nie, S.; Cai, H.; Zhang, G.; Cui, S. W.; Xie,
M.; Phillips, G. O. Study on Dendrobium Officinale O-Acetyl-
Glucomannan (Dendronan®): Part IV. Immunomodulatory
Activity in Vivo. J. Funct. Foods 2015, 15, 525–532.
(41)
Haario, H. Modest 6.0- A Users’s Guide. ProMath:
Helsinki 2001.
(42) Staroverov, V. N.; Scuseria, G. E.; Tao, J.; Perdew, J. P.
Comparative Assessment of
a New Nonempirical Density
Functional: Molecules and Hydrogen-Bonded Complexes. J.
Chem. Phys. 2003, 119, 12129–12137.
(43) Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. A
Consistent and Accurate Ab Initio Parametrization of Density
Functional Dispersion Correction (DFT-D) for the 94 Elements
H-Pu. J. Chem. Phys. 2010, 132, 154104.
(44) Becke, A. D.; Johnson, E. R. A Density-Functional
Model of the Dispersion Interaction. J. Chem. Phys. 2005, 123,
154101.
(45) Grimme, S.; Ehrlich, S.; Goerigk, L. Effect of the
Damping Function in Dispersion Corrected Density Functional
Theory. J. Comput. Chem. 2011, 32, 1456–1465.
(46) Weigend, F.; Ahlrichs, R. Balanced Basis Sets of Split
Valence, Triple Zeta Valence and Quadruple Zeta Valence
Quality for H to Rn: Design and Assessment of Accuracy. Phys.
Chem. Chem. Phys. 2005, 7, 3297–3305.
(47) Rappoport, D.; Furche, F. Property-Optimized
Gaussian Basis Sets for Molecular Response Calculations. J.
Chem. Phys. 2010, 133, 134105.
(48) Plessow, P. Reaction Path Optimization without NEB
Springs or Interpolation Algorithms. J. Chem. Theory Comput.
2013, 9, 1305–1310.
(49) Klamt, A.; Schüürman, G. Cosmo - a New Approach To
Dielectric Screening in Solvents With Explicit Expressions for
the Screening Energy and Its Gradient. J. Chem. Soc. Trans. 2
1993, 799–805.
(24) Willför, S.; Sundberg, K.; Tenkanen, M.; Holmbom, B.
Spruce-Derived Mannans
- A Potential Raw Material for
Hydrocolloids and Novel Advanced Natural Materials.
Carbohydr. Polym. 2008, 72, 197–210.
(25) Willför, S.; Sundberg, A.; Pranovich, A.; Holmbom, B.
Polysaccharides in Some Industrially Important Hardwood
Species. Wood Sci. Technol. 2005, 39, 601–617.
(26) Ebringerová, A.; Hromádková, Z.; Hříbalová, V.; Xu, C.;
Holmbom, B.; Sundberg, A.; Willför, S. Norway Spruce
Galactoglucomannans Exhibiting Immunomodulating and
Radical-Scavenging Activities. Int. J. Biol. Macromol. 2008, 42, 1–
5.
(27) Portaleone, P. Acetylation. In Encyclopedia of
Endocrine Diseases; Elsevier, 2004; pp 9–12.
(28) Fischer, E. Wanderung von Acyl Bei Den Glyceriden.
Ber. Dtsch. Chem. Ges. 1920, 53, 1621–1633.
(29) Roslund, M. U.; Aitio, O.; Wärna, J.; Maaheimo, H.;
Murzin, D. Y.; Leino, R. Acyl Group Migration and Cleavage in
Selectively Protected β-D-Galactopyranosides as Studied by NMR
Spectroscopy and Kinetic Calculations. J. Am. Chem. Soc. 2008,
130, 8769–8772.
(30) Brecker, L.; Manut, M.; Schwarz, A.; Nidetzky, B. In
Situ Proton NMR Study of Acetyl and Formyl Group Migration
in Mono-O-Acyl D-Glucose. Magn. Reson. Chem. 2009, 47, 328–
332.
(50) Riplinger, C.; Pinski, P.; Becker, U.; Valeev, E. F.;
Neese, F. Sparse Maps - A Systematic Infrastructure for Reduced-
Scaling Electronic Structure Methods. II. Linear Scaling Domain
Based Pair Natural Orbital Coupled Cluster Theory. J. Chem.
Phys. 2016, 144, 024109.
(31)
Yoshimoto, K.; Tsuda, Y. General Path of O-Acyl
Migration in d-Glucose Derivatives: Acyl Migration of Methyl
Mono-O-Myristoyl-α- and β-D-Glucopyranosides and Mono-O-
Myristoyl-D-Glucopyranoses. Chem. Pharm. Bull. 1983, 31, 4324–
4334.
(32) Ohara, K.; Lin, C. C.; Yang, P. J.; Hung, W. T.; Yang, W.
Bin; Cheng, T. J. R.; Fang, J. M.; Wong, C. H. Synthesis and
Bioactivity of β-(1→4)-Linked Oligomannoses and Partially
Acetylated Derivatives. J. Org. Chem. 2013, 78, 6390–6411.
(33) Puchart, V.; Agger, J. W.; Berrin, J. G.; Várnai, A.;
Westereng, B.; Biely, P. Comparison of Fungal Carbohydrate
(51)
Halkier, A.; Helgaker, T.; Jørgensen, P.; Klopper, W.;
Koch, H.; Olsen, J.; Wilson, A. K. Basis-Set Convergence in
Correlated Calculations on Ne, N2, and H2O. Chem. Phys. Lett.
1998, 286, 243–252.
(52) Klamt, A. Conductor-like Screening Model for Real
Solvents: A New Approach to the Quantitative Calculation of
Solvation Phenomena. J. Phys. Chem. 1995, 99, 2224–2235.
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