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Volumn 73, Issue 4, 2008, Pages 1371-1378

New deuterated oligo(ethylene glycol) building blocks and their use in the preparation of surface active lipids possessing labeled hydrophilic tethers

Author keywords

[No Author keywords available]

Indexed keywords

COUPLING REACTIONS; DITOSYLATES; SPACER GROUP;

EID: 39349095820     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701979z     Document Type: Article
Times cited : (14)

References (105)
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    • Becucci, L.; Moncelli, M. R.; Guidelli, R. Langmuir 2006, 22, 1341-1346.
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    • Plech, A.; Salditt, T. In Handbook of Polyelectrolytes and Their Applications; Tripathy, S. K., Kumar, J., Nalwa, H. S., Eds.; American Scientific Publishers: Stevenson Ranch, CA, 2002; 1, pp 265-291.
    • Plech, A.; Salditt, T. In Handbook of Polyelectrolytes and Their Applications; Tripathy, S. K., Kumar, J., Nalwa, H. S., Eds.; American Scientific Publishers: Stevenson Ranch, CA, 2002; Vol. 1, pp 265-291.
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    • An efficient and useful synthesis of a functionalized dimeric EG2-d8 unit that does not begin with EG-d4 has been described: see ref 31. A deuterated poly(ethylene glycol) material has been prepared. See: Poschalko, A, Lancelot, N, Marin, J, Larras, V, Limal, D, Elbayed, K, Raya, J, Piotto, M, Briand, J.-P, Guichard, G, Bianco, A. Chemistry (Weinheim) 2004, 10, 4532-4537
    • 4 has been described: see ref 31. A deuterated poly(ethylene glycol) material has been prepared. See: Poschalko, A.; Lancelot, N.; Marin, J.; Larras, V.; Limal, D.; Elbayed, K.; Raya, J.; Piotto, M.; Briand, J.-P.; Guichard, G.; Bianco, A. Chemistry (Weinheim) 2004, 10, 4532-4537.
  • 77
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    • At the time of these experiments, no oligomeric forms of EG-d4 were commercially available
    • 4 were commercially available.
  • 83
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    • Chang, Y.; Wang, Z.; Notter, Robert, H.; Wang, Z.; Qu, L.; Schwan, A. L. Bioorg. Med. Chem. Lett. 2004, 14, 5983-5986.
    • (b) Chang, Y.; Wang, Z.; Notter, Robert, H.; Wang, Z.; Qu, L.; Schwan, A. L. Bioorg. Med. Chem. Lett. 2004, 14, 5983-5986.
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    • This value arises in the following manner: 52% losses occur in the two steps providing ditosylate 3-d8 and 35% losses occur making 3-d4. Since these components each deliver one-half of the required four EG units to 6-d16, those losses become 26% and 17.5, respectively. The total losses are therefore 43.5% before the final two near-quantitative steps completing the preparation of EG4-d16
    • 16.
  • 87
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    • It was felt that employing one end of EG4 as a nucleophile under harsh basic conditions may bring about its breakdown. Hence monoprotection schemes of commercial EG4 (protiated form) were investigated for eventual creation of electrophilic EG4 derivatives.
    • It was felt that employing one end of EG4 as a nucleophile under harsh basic conditions may bring about its breakdown. Hence monoprotection schemes of commercial EG4 (protiated form) were investigated for eventual creation of electrophilic EG4 derivatives.
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    • A few trials with the mesylate of diphytanyl glycerol and a monoproptected EG4 derivative gave no reaction and this option was discarded.
    • A few trials with the mesylate of diphytanyl glycerol and a monoproptected EG4 derivative gave no reaction and this option was discarded.
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    • 16, the effective yield was 93%.
    • 16, the effective yield was 93%.
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    • Becucci, L.; Guidelli, R.; Karim, C. B.; Thomas, D. D.; Veglia, G. Biophys. J. 2007, 93, 2678-2687.
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    • Becucci, L.; Santucci, A.; Guidelli, R. J. Phys. Chem. B, 2007, 111, 9814-9820.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.