Correction to: Towards lignin-protein crosslinking: amino acid adducts of a lignin model quinone methide (Cellulose, (2014), 21, 3, (1395-1407), 10.1007/s10570-014-0181-y);Towards lignin-protein crosslinking: Amino acid adducts of a lignin model quinone methide

Cellulose

Volumn 21, Issue 3, 2014, Pages 1395-1407

  Diehl, Brett G ^a   Watts, Heath D ^b   Kubicki, James D ^b   Regner, Matthew R ^c   Ralph, John ^c   Brown, Nicole R ^a  

^a University Park   (United States)

^b PENNSYLVANIA STATE UNIVERSITY   (United States)

^c USA   (United States)

Author keywords

Amino acid; Crosslinking; Density functional theory; Lignin; Nuclear magnetic resonance spectroscopy; Protein; Quinone methide

Indexed keywords

AMINO ACIDS; CROSSLINKING; DENSITY FUNCTIONAL THEORY; HYDROXYPROLINE; ISOMERS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANTS (BOTANY); PROTEINS; QUINONE; REACTION INTERMEDIATES;

2D NUCLEAR MAGNETIC RESONANCES; HIGH-MOLECULAR WEIGHT POLYMERS; LIGNIN CARBOHYDRATES; LIGNIN MODEL COMPOUND; LIGNIN POLYMERIZATION; LIGNOCELLULOSIC MATERIAL; PROTEIN CROSSLINKING; QUINONE METHIDE;

LIGNIN;

EID: 84901192832     PISSN: 09690239     EISSN: 1572882X     Source Type: Journal    
DOI: 10.1007/s10570-019-02493-y     Document Type: Erratum

References (64)

1. Adamo C, Barone V (1998) Exchange functionals with improved long-range behavior and adiabatic connection methods without adjustable parameters: the mPW and mPW1PW models. J Chem Phys 108: 664-675.
2. Albersheim P, Darvill A, Roberts K, Sederoff R, Staehelin A (2010) Principles of cell wall architecture and assembly. In: Plant cell walls. Garland Science, New York, New York, pp 227-272.
3. Awad HM, Boersma MG, Vervoort J, Rietjens IMCM (2000) Peroxidase-catalyzed formation of quercetin quinone methide-glutathione adducts. Arch Biochem Biophys 378: 224-233.
4. Balakshin M, Capanema E, Gracz H, Chang H, Jameel H (2011) Quantification of lignin-carbohydrate linkages with high-resolution NMR spectroscopy. Planta 233: 1097-1110.
5. 13C NMR chemical shifts. Chem Eur J 8(14): 3240-3245.
6. Beat K, Templeton MD, Lamb CJ (1989) Specific localization of a plant cell wall glycine-rich protein in protoxylem cells of the vascular system. Proc Natl Acad Sci USA 86: 1529-1533.
7. Boerjan W, Ralph J, Baucher M (2003) Lignin biosynthesis. Ann Rev Plant Biol 54: 519-546.
8. Bolton JL, Turnipseed SB, Thompson JA (1997) Influence of quinone methide reactivity on the alkylation of thiol and amino groups in proteins: studies utilizing amino acid and peptide models. Chem Biol Interact 107: 185-200.
9. Buhl M, Kaupp M, Malkina OL, Malkin VG (1999) The DFT route to NMR chemical shifts. J Comput Chem 20: 91-105.
10. Cances E, Mennucci B, Tomasi J (1997) A new integral equation formalism for the polarizable continuum model: theoretical background and applications to isotropic and anisotropic dielectrics. J Chem Phys 107(8): 3032-3041.
11. Capanema EA, Balakshin MY, Kadla JF (2004) A comprehensive approach for quantitative lignin characterization by NMR spectroscopy. J Agric Food Chem 52: 1850-1860.
12. Cassab IG, Varner JE (1988) Cell wall proteins. Ann Rev Plant Physiol Plant Mol Biol 39: 321-353.
13. Chapple C, Ladisch M, Meilan R (2007) Loosening lignin's grip on biofuel production. Nat Biotechnol 25: 746-748.
14. Cheeseman JR, Trucks GW, Keith TA, Frisch MJ (1996) A comparison of models for calculating nuclear magnetic resonance shielding tensors. J Chem Phys 104: 5497-5509.
15. Chen F, Dixon RA (2008) Genetic manipulation of lignin biosynthesis to improve biomass characteristics for agro-industrial processes. In Vitro Cell Dev Biol Anim 44: S28-S29.
16. Clark T, Chandrasekhar J, Spitznagel GW, Schleyer PVR (1983) Efficient diffuse function-augmented basis sets for anion calculations. III. The 3-21 + G basis set for first-row elements, Li-F. J Comput Chem 4(3): 294-301.
17. Cosgrove D (2005) Growth of the plant cell wall. J Nat Rev Mol Cell Biol 6: 850-861.
18. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA (2009) Gaussian 09, revision B01. Gaussian, Inc, Wallingford.
19. Gogonea V (1998) Self-consistent reaction field methods: cavities. In: Schleyer PVR, Schreiner PR, Allinger NL, Clark T, Gasteiger J, Kollman P, Schaefer HF III (eds) Encyclopedia of computational chemistry. Wiley, New York, pp 2560-2574.
20. Gottlieb HE, Kotlyar V, Nudelman A (1997) NMR chemical shifts of common laboratory solvents as trace impurities. J Org Chem 62(21): 7512-7515.
21. Harrak H, Chamberland H, Plante M, Bellemare G, Lafontaine JG, Tabaeizadeh Z (1991) A proline-, threonine-, and glycine-rich protein down-regulated by drought is localized in the cell wall of xylem elements. Plant Phys 121: 557-564.
22. Hohenberg P, Kohn W (1964) Inhomgeneous electron gas. Phys Rev 136(3b): B864-B871.
23. Jose M, Puigdomenech P (1993) Structure and expression of genes encoding for structural proteins of the plant cell wall. New Phytol 125: 259-282.
24. Jung HG (1989) Forage lignins and their effects on fiber digestibility. Agron J 81: 33-38.
25. Jung HG, Allen MS (1995) Characteristics of plant cell walls affecting intake and digestibility of forages by ruminants. J Anim Sci 73: 2774-2790.
26. Karadakov PB (2008) Ab initio calculation of NMR shielding constants. In: Webb GA (ed) Modern magnetic resonance. Springer, New York, pp 63-70.
27. Kawai S, Okita K, Sugishita K, Tanaka A, Ohashi H (1999) Simple method for synthesizing phenolic β-O-4 dilignols. J Wood Sci 45: 440-443.
28. Kieliszewski M, Lamport DTA, Tan L, Cannon MC (2011) Hydroxyproline-rich glycoproteins: form and function. Ann Plant Rev 41: 321-342.
29. 5. Org Biomol Chem 8: 576-591.
30. Kohn W, Sham LJ (1965) Self-consistent equations including exchange and correlation effects. Phys Rev 140(4A): A1133-A1138.
31. Krishnan RBJS, Binkley JS, Seeger R, Pople JA (1980) Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions. J Chem Phys 72: 650.
32. 14C labeled 3-methoxy-4-hydroxy-α-(2-methoxy-phenoxy)-β-hydroxypropiophenone, a lignin model compound. Holzforschung 35: 66-69.
33. Leary GJ (1980) Quinone methides and the structure of lignin. Wood Sci Technol 14: 21-34.
34. Leary G, Miller IJ, Thomas W, Woolhouse AD (1977) The chemistry of reactive lignin intermediates. Part 5. Rates of reactions of quinone methides with water, alcohols, phenols, and carboxylic acids. J Chem Soc, Perkin Trans 2 13: 1737-1739.
35. Li X, Weng JK, Chapple C (2008) Improvement of biomass through lignin modification. Plant J 54: 569-581.
36. Liang H, Frost CJ, Wei X, Brown NR, Carlson JE, Tien M (2008) Improved sugar release from lignocellulosic material by introducing a tyrosine-rich cell wall peptide gene in poplar. Clean 36(8): 662-668.
37. 13C chemical shifts: a useful tool for natural product, mechanistic, and synthetic organic chemistry. Chem Rev 112(3): 1839-1862.
38. Mansfield SD, Kim H, Lu F, Ralph J (2012) Whole plant cell wall characterization using solution-state 2D NMR. Nat Protoc 7(9): 1579-1589.
39. McQueen-Mason S, Cosgrove D (1994) Disruption of hydrogen bonding between plant cell wall polymers by proteins that induce wall extension. J Proc Natl Acad Sci USA 91: 6574-6578.
40. Miyagawa Y, Takemoto O, Takano T, Kamitakahara H, Nakatsubo F (2012) Fractionation and characterization of lignin carbohydrate complexes (LCCs) of Eucalyptus globulus in residues left after MWL isolation. Part I: analyses of hemicellulose-lignin fractionation (HC-L). Holzforschung 66: 459-465.
41. Mostaghni F, Abbas T, Seyed AM (2013) Synthesis, spectroscopic characterization and DFT calculations of β-O-4 type lignin model compounds. Spectrochimica Acta Part A Mol Biomol Spec 110: 430-436.
42. Nagy PI, Tejada FR, Messer WS (2005) Theoretical studies of the tautomeric equilibria for five-member N-heterocycles in the gas phase and in solution. J Phys Chem 109: 22588-22602.
43. Papajak E, Zheng J, Xu X, Leverentz HR, Truhlar DG (2011) Perspectives on basis sets beautiful: seasonal plantings of diffuse basis functions. J Chem Theory Comput 7(10): 3027-3034.
44. Ralph J, Young RA (1983) Stereochemical aspects of addition reactions involving lignin model quinone methides. J Wood Chem Technol 3(2): 161-181.
45. Ralph J, Lundquist K, Brunow G, Lu F, Kim H, Schatz PF, Marita JM, Hatfield RD, Ralph SA, Christensen JH (2004a) Lignins: natural polymers from oxidative coupling of 4-hydroxyphenylpropanoids. Phytochem Rev 3: 29-60.
46. Ralph SA, Ralph J, Landucci LL (2004) NMR database of lignin and cell wall model compounds. http://ars. usda. gov/Services/docs. htm?docid=10491 Accessed 27 Sept 2013.
47. Ralph J, Schatz PF, Lu F, Kim H, Akiyama T, Nelsen SF (2009) Quinone methides in lignification. In: Rokita SE (ed) Quinone methides. Wiley, New Jersey, pp 385-420.
48. Ramakrishnan K, Fisher J (1983) Nucleophilic trapping of 7, 11-dideoxyanthracyclinone quinone methides. J Am Chem Soc 105: 7187-7188.
49. Ryser U, Schorderet M, Zhao G, Studer D, Ruel K, Hauf G, Keller B (1997) Structural cell-wall proteins in protoxylem development: evidence for a repair process mediated by a glycine-rich protein. Plant J 12(1): 97-111.
50. 13C NMR calculations. J Org Chem 74(19): 7254-7260.
51. Sarotti AM, Pellegrinet SC (2012) Application of the multi-standard methodology for calculating (1)H NMR chemical shifts. J Org Chem 77(14): 6059-6065.
52. Schreckenbach G, Ziegler T (1995) Calculation of NMR shielding tensors using gauge-including atomic orbitals and modern density functional theory. J Chem Phys 99(2): 606-611.
53. Stewart JJ, Kadla JF, Mansfield SD (2006) The influence of lignin chemistry and ultrastructure on the pulping efficiency of clonal aspen (Populus termuloides Michx). Holzforschung 60: 111-122.
54. Terashima N, Atalla RH, Ralph SA, Landucci LL, Lapierre C, Monties B (1995) New preparations of lignin polymer models under conditions that approximate cell wall lignification. Holzforschung 49: 521-527.
55. Toikka M, Jussi S, Teleman A, Brunow G (1998) Lignin-carbohydrate model compounds. Formation of lignin-methyl arabinoside and lignin-methyl galactoside benzyl ethers via quinone methide intermediates. J Chem Soc, Perkin Trans 1 1: 3813-3818.
56. Vanholme R, Morreel K, Ralph J, Boerjan W (2010) Lignin biosynthesis and structure. Plant Phys 153: 895-905.
57. Watts HD, Mohamed MNA, Kubicki JD (2011) Comparison of multistandard and TMS-standard calculated NMR shifts for coniferyl alcohol and application of the multistandard method to lignin dimers. J Phys Chem B 115(9): 1958-1970.
58. Whitmore FW (1978a) Lignin-carbohydrate complex formed in isolated cell walls of callus. Phytochem 17: 421-425.
59. Whitmore FW (1978b) Lignin-protein complex catalyzed by peroxidase. Plant Sci Lett 13: 241-245.
60. Whitmore FW (1982) Lignin-protein complex in cell walls of Pinus elliottii: amino acid constituents. Phytochem 21(2): 315-318.
61. Wolinski K, Hinton JF, Pulay P (1990) Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. J Am Chem Soc 112(23): 8251-8260.
62. Xu Y, Chen C, Thomas TP, Azadi P, Diehl B, Tsai C, Brown N, Carlson JE, Tien M, Liang H (2013) Wood chemistry analysis and expression profiling of a poplar clone expressing a tyrosine-rich peptide. Plant Cell Rep 32: 1827-1841.
63. 13C and 2D HSQC NMR spectroscopy. J Agric Food Chem 59: 10604-10614.
64. Zhao Y, Shultz NE, Truhlar DG (2006) Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions. J Chem Theory Comput 2(2): 364-382.