DOI: 10.1016/s0040-4039(00)00452-4. Proteinase N-catalysed transesterifications in DMSO–water and DMF–water: preparation of sucrose monomethacrylate

Proteinase N-catalysed transesterifications in DMSO–water and DMF–water: preparation of sucrose monomethacrylate

10.1016/s0040-4039(00)00452-4

Crossref journal-article

Elsevier BV

Tetrahedron Letters (78)

Bibliography

Potier, P., Bouchu, A., Descotes, G., & Queneau, Y. (2000). Proteinase N-catalysed transesterifications in DMSOâwater and DMFâwater: preparation of sucrose monomethacrylate. Tetrahedron Letters, 41(19), 3597â3600.

Authors 4

Pierre Potier (first)
Alain Bouchu (additional)
Gérard Descotes (additional)
Yves Queneau (additional)

References 21 Referenced 30

Klibanov, A. M. Chemtech. 1986, 354–359.
Zaks, A. In Biocatalysts for Industry; Dordick, J. S., Ed.; Plenum Press: New York, 1991; pp. 161–180. (10.1007/978-1-4757-4597-9_8)
Dordick, J. S. Biotechnol. Prog. 1992, 8, 259–267. (10.1021/bp00016a001)
Riva, S. In Carbohydrate Polyesters as Fat Substitutes; Akoh, C. C.; Swanson, B. G., Eds.; M. Dekker Inc.: New York, 1994; pp. 37–64.
Coulon, D.; Ghoul, M. Agro-Food-Ind. Hi-Tech 1998, 9, 22–26; Chem. Abs. 1999, 130, 97178c.
de Goede, A. T. J. W.; Woudenberg-van Oosterom, M.; van Rantwijk, F. Carbohydrates in Europe 1994, 10, 18–20.
Woudenberg-van Oosterom, M.; van Rantwijk, F.; Sheldon, R. A. Biotech. Bioing. 1996, 49, 328–333. (10.1002/(SICI)1097-0290(19960205)49:3<328::AID-BIT11>3.0.CO;2-A)
Riva, S.; Chopineau, J.; Kieboom, A. P. G.; Klibanov, A. M. J. Am. Chem. Soc. 1988, 110, 584–589. (10.1021/ja00210a045)
Carrea, G.; Riva, S.; Secundo, F.; Danieli, B. J. Chem. Soc., Perkin Trans. 1 1989, 1057–1061. (10.1039/P19890001057)
Mentech, J.; Betremieux, I.; Legger, B. Eur. Pat. Appl. EP 467,762, 1992; Chem. Abstr. 1992, 116, 256232v.
Jhurry, D.; Deffieux, A.; Fontanille, M.; Betremieux, I.; Mentech, J.; Descotes, G. Makromol. Chem. 1992, 193, 2997–3007. (10.1002/macp.1992.021931206)
Gruber, H.; Greber, G. Zuckerindustrie 1990, 115, 476–483.
Chan, A. W.-Y.; Ganem, B. Biocatalysis 1993, 8, 163–169. (10.3109/10242429308998203)
Zaks, A.; Klibanov, A. M. J. Biol. Chem. 1988, 263, 8017–8021.
Affleck, R.; Xu, Z.-F.; Suzawa, V.; Focht, K.; Clark, D. S.; Dordick, J. S. Proc. Natl. Acad. Sci. USA 1992, 89, 1100–1104. (10.1073/pnas.89.3.1100)
Halling, P. J. Enzyme Microb. Technol. 1994, 16, 178–206. (10.1016/0141-0229(94)90043-4)
1′-O-Butyryl sucrose (2a): [α]D20 +62 (c 1, MeOH); 1H NMR (CD3OD, 300 MHz) δ (ppm) 5.44 (d, 1H, J1,2=3.5 Hz, H-1), 4.43 (d, 1H, J1′a,b=12.1 Hz, H-1′a), 4.25 (d, 1H, J1′a,b=11.9 Hz, H-1′b), 4.15 (d, 1H, J3′–4′=8.7 Hz, H-3′), 4.09 (t, 1H, J4′,5′=8.4 Hz, H-4′), 3.9–3.6 (m, 7H, H-3, H-5, H-6ab, H-5′, H-6′ab), 3.4 (dd, 1H, J2,1=3.5 Hz, J2,3=9.8 Hz, H-2), 3.3 (t, 1H, J3,4=9.3 Hz, H-4), 2.4 (t, 2H, J=7.35 Hz, CH2), 1.7 (m, 2H, CH2), 1.0 (t, 3H, J=7.35 Hz, CH3); 13C NMR (CD3OD, 75 MHz) δ (ppm) 173.6 (CO), 104.5 (C-2′), 93.1 (C-1), 82.7 (C-5′), 77.7 (C-3′), 73.9 (C-4′), 73.5 (C-5), 73.4 (C-3), 72.0 (C-2), 70.0 (C-4), 62.7 (C-1′), 62.2 (C-6′), 61.2 (C-6), 35.9, 18.4 (2 CH2), 13.0 (1 CH3). Anal. calcd for C16H28O12+1.1 H2O: C, 44.5; H, 7.1; found: C, 44.4; H, 7.3. HRMS (FAB+) m/z calcd: 435.1478, found: 435.1481 (13C NMR, see Ref. 8).
Weber, H. K.; Faber, K. Methods Enzymol. 1997, 286, 509–518. (10.1016/S0076-6879(97)86026-0)
Zaks, A.; Klibanov, A. M. J. Biol. Chem. 1988, 263, 3194–3201.
Burke, P. A. J. Am. Chem. Soc. 1989, 111, 8290–8291. (10.1021/ja00203a046)
Polat, T.; Bazin, H. G.; Linhardt, R. J. J. Carbohydr. Chem. 1997, 16, 1319–1325. (10.1080/07328309708005752)

Dates

Type	When
Created	23 years, 1 month ago (July 25, 2002, 10:34 p.m.)
Deposited	6 years, 4 months ago (April 14, 2019, 8:54 a.m.)
Indexed	1 year, 3 months ago (May 28, 2024, 3:29 p.m.)
Issued	25 years, 3 months ago (May 1, 2000)
Published	25 years, 3 months ago (May 1, 2000)
Published Print	25 years, 3 months ago (May 1, 2000)

Funders 0

None

BibTeX

@article{Potier_2000, title={Proteinase N-catalysed transesterifications in DMSO–water and DMF–water: preparation of sucrose monomethacrylate}, volume={41}, ISSN={0040-4039}, url={http://dx.doi.org/10.1016/s0040-4039(00)00452-4}, DOI={10.1016/s0040-4039(00)00452-4}, number={19}, journal={Tetrahedron Letters}, publisher={Elsevier BV}, author={Potier, Pierre and Bouchu, Alain and Descotes, Gérard and Queneau, Yves}, year={2000}, month=may, pages={3597–3600} }

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