Redistribution of acetyl groups on the non-reducing end xylopyranosyl residues and their removal by xylan deacetylases
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| 024 | 7 | 0 | |a 10.1007/s00253-014-6160-2 |2 doi |
| 035 | |a (NATIONALLICENCE)springer-10.1007/s00253-014-6160-2 | ||
| 245 | 0 | 0 | |a Redistribution of acetyl groups on the non-reducing end xylopyranosyl residues and their removal by xylan deacetylases |h [Elektronische Daten] |c [Vladimír Puchart, Peter Biely] |
| 520 | 3 | |a Background: Monoacetylated xylosyl residues of the main hardwood hemicellulose acetylglucuronoxylan undergo acetyl group migration between positions 2 and 3, and predominantly to position 4 of the non-reducing end xylopyranosyl (NRE-Xylp) residues which are amplified by saccharifying enzymes. On monoacetylated non-reducing end xylopyranosyl (NRE-Xylp) residues of xylooligosaccharides the acetyl group migrates predominantly to position 4 and hinders their hydrolysis by β-xylosidase. Methods: Acetyl migration on the NRE-Xylp residues and their enzymatic deacetylation by various xylan deacetylases was followed by 1H-NMR spectroscopy and TLC. Results: A 5-min heat treatment of 4-nitrophenyl 3-O-acetyl-β-D-xylopyranoside was sufficient to establish equilibrium between monoacetate derivatives acetylated at positions 2, 3 and 4. Rapid acetyl migration along the NRE-Xylp ring at elevated temperature was confirmed in derivatives of methyl β-1,4-xylotrioside (Xyl3Me) monoacetylated solely on the NRE-Xylp residue, the analogues of naturally occurring acetylated xylooligosaccharides. The Xyl3Me monoacetates were used as substrates to study regioselectivity of the NRE-Xylp residue deacetylation by various acetylxylan esterases (AcXEs) of distinct carbohydrate esterase (CE) families. CE1, CE4 and CE6 AcXEs hydrolyzed considerably faster the 2″-O-acetyl derivative than the 3″-O-acetyl derivative. In contrast, the CE16 acetyl esterase preferred to attack the ester bond at position 3 followed by position 4. Conclusions: Redistribution of acetyl group on the NRE-Xylp residues is extremely rapid at elevated temperature and includes the formation of 4-acetate. Regioselectivity of AcXEs and CE16 acetyl esterase on these monoacetates is complementary. General significance: The formation of all isomers of acetylated xylosyl residues must be taken into account after a long-term incubation of acetylxylan and acetylated xylooligosaccharides solutions or upon their treatment at elevated temperatures. This phenomenon emphasizes requirement of both types of xylan deacetylases to enable a rapid saccharification of xylooligosaccharides by glycoside hydrolases. | |
| 540 | |a Springer-Verlag Berlin Heidelberg, 2014 | ||
| 690 | 7 | |a Xylooligosaccharide deacetylation |2 nationallicence | |
| 690 | 7 | |a Regioselectivity |2 nationallicence | |
| 690 | 7 | |a Acetylxylan esterase |2 nationallicence | |
| 690 | 7 | |a Non-reducing end deacetylase |2 nationallicence | |
| 690 | 7 | |a Monoacetates of methyl β-1,4-xylotrioside |2 nationallicence | |
| 690 | 7 | |a Acetyl group migration |2 nationallicence | |
| 690 | 7 | |a CE : Carbohydrate esterase |2 nationallicence | |
| 690 | 7 | |a AcXE : Acetylxylan esterase |2 nationallicence | |
| 690 | 7 | |a AcE : Acetyl esterase |2 nationallicence | |
| 690 | 7 | |a Xyl3Me : Methyl β-D-xylopyranosyl-1,4-β-D-xylopyranosyl-1,4-β-D-xylopyranoside, methyl β-D-xylotrioside |2 nationallicence | |
| 690 | 7 | |a Xyl p : β-D-xylopyranosyl |2 nationallicence | |
| 690 | 7 | |a MeGlcA : 4-O-methyl-α-D-glucuronic acid |2 nationallicence | |
| 700 | 1 | |a Puchart |D Vladimír |u Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, 845 38, Bratislava, Slovak Republic |4 aut | |
| 700 | 1 | |a Biely |D Peter |u Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, 845 38, Bratislava, Slovak Republic |4 aut | |
| 773 | 0 | |t Applied Microbiology and Biotechnology |d Springer Berlin Heidelberg |g 99/9(2015-05-01), 3865-3873 |x 0175-7598 |q 99:9<3865 |1 2015 |2 99 |o 253 | |
| 856 | 4 | 0 | |u https://doi.org/10.1007/s00253-014-6160-2 |q text/html |z Onlinezugriff via DOI |
| 898 | |a BK010053 |b XK010053 |c XK010000 | ||
| 900 | 7 | |a Metadata rights reserved |b Springer special CC-BY-NC licence |2 nationallicence | |
| 908 | |D 1 |a research-article |2 jats | ||
| 949 | |B NATIONALLICENCE |F NATIONALLICENCE |b NL-springer | ||
| 950 | |B NATIONALLICENCE |P 856 |E 40 |u https://doi.org/10.1007/s00253-014-6160-2 |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Puchart |D Vladimír |u Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, 845 38, Bratislava, Slovak Republic |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Biely |D Peter |u Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, 845 38, Bratislava, Slovak Republic |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t Applied Microbiology and Biotechnology |d Springer Berlin Heidelberg |g 99/9(2015-05-01), 3865-3873 |x 0175-7598 |q 99:9<3865 |1 2015 |2 99 |o 253 | ||