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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 20
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Original Articles

Chlorotrimethylsilane Mediated Formation of ω-Allyl Esters of Aspartic And Glutamic Acids

Peter J. Belshaw Department of Chemistry, University of Waterloo, Waterloo, Ont., Canada, N2L 3G1
,
Shadreck Mzengeza Department of Chemistry, University of Waterloo, Waterloo, Ont., Canada, N2L 3G1
&
Gilles A. Lajoie Department of Chemistry, University of Waterloo, Waterloo, Ont., Canada, N2L 3G1
Pages 3157-3160 | Received 23 Aug 1990, Published online: 24 Oct 2006

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Young S. Rho, Siho Park, Wan-Joong Kim, Gyuil Kim, Dong Jin Yoo, Heun-Soo Kang & Soon-Ryang Chung. (2002) SYNTHESIS OF NEW ANTHRACYCLINE DERIVATIVES CONTAINING PYRUVIC, ASPARTIC, OR N-ACETYLASPARTIC ACID MOLECULE. Synthetic Communications 32:13, pages 1961-1975.
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V. Bavetsias, G.M. F. Bisset & M. Jarman. (1995) Convenient Preparation of α-Tert-Butyl N-Blocked Glutamates Through γ-Allyl Ester Protection. Synthetic Communications 25:7, pages 947-958.
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Anna Crivici & Gilles Lajoie. (1993) A Procedure for the Large Scale Preparation of Nε-Alloc-lysine and Nε-Alloc-Nα-Fmoc-lysine. Synthetic Communications 23:1, pages 49-53.
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Tan P. Nguyen, Alexandra D. Easley, Nari Kang, Sarosh Khan, Soon-Mi Lim, Yohannes H. Rezenom, Shaoyang Wang, David K. Tran, Jingwei Fan, Rachel A. Letteri, Xun He, Lu Su, Cheng-Han Yu, Jodie L. Lutkenhaus & Karen L. Wooley. (2021) Polypeptide organic radical batteries. Nature 593:7857, pages 61-66.
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Tomohiro Takaishi, Minoru Izumi, Ryo Ota, Chieri Inoue, Hiromasa Kiyota & Koichi Fukase. (2017) Product Selectivity of Esterification of L-Aspartic Acid and L-Glutamic Acid Using Chlorotrimethylsilane. Natural Product Communications 12:2, pages 1934578X1701200.
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Alexandrina Nan & Ioana Coralia Feher. A new polyester based on allyl α-hydroxy glutarate as shell for magnetite nanoparticles. A new polyester based on allyl α-hydroxy glutarate as shell for magnetite nanoparticles.
Amanda C. Engler, Anita Shukla, Sravanthi Puranam, Hilda G. Buss, Nina Jreige & Paula T. Hammond. (2011) Effects of Side Group Functionality and Molecular Weight on the Activity of Synthetic Antimicrobial Polypeptides. Biomacromolecules 12:5, pages 1666-1674.
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Benedikt Sammet, Tobias Bogner, Markus Nahrwold, Christine Weiss & Norbert Sewald. (2010) Approaches for the Synthesis of Functionalized Cryptophycins. The Journal of Organic Chemistry 75:20, pages 6953-6960.
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Amanda C. Engler, Hyung‐il Lee & Paula T. Hammond. (2009) Highly Efficient “Grafting onto” a Polypeptide Backbone Using Click Chemistry. Angewandte Chemie International Edition 48:49, pages 9334-9338.
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Amanda C. Engler, Hyung‐il Lee & Paula T. Hammond. (2009) Highly Efficient “Grafting onto” a Polypeptide Backbone Using Click Chemistry. Angewandte Chemie 121:49, pages 9498-9502.
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Albert Isidro-Llobet, Mercedes Álvarez & Fernando Albericio. (2009) Amino Acid-Protecting Groups. Chemical Reviews 109:6, pages 2455-2504.
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Timo Nuijens, John A.W. Kruijtzer, Claudia Cusan, Dirk T.S. Rijkers, Rob M.J. Liskamp & Peter J.L.M. Quaedflieg. (2009) A versatile and selective chemo-enzymatic synthesis of β-protected aspartic and γ-protected glutamic acid derivatives. Tetrahedron Letters 50:23, pages 2719-2721.
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Lutz Tietze, Olaf Panknin, Birgit Krewer, Felix Major & Ingrid Schuberth. (2008) Synthesis and Biological Evaluation of a Novel Pentagastrin- Toxin Conjugate Designed for a Targeted Prodrug Monotherapy of Cancer. International Journal of Molecular Sciences 9:5, pages 821-837.
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Mare Cudic & Gregg B. Fields. 2008. Molecular Biomethods Handbook. Molecular Biomethods Handbook 515 546 .
George Barany, Nancy Kneib-Cordonier & Daniel G. Mullen. 2002. Encyclopedia of Polymer Science and Technology. Encyclopedia of Polymer Science and Technology.
Balazs Hargittai, Yongxin Han, Steven A. Kates & George Barany. 2002. Peptides Frontiers of Peptide Science. Peptides Frontiers of Peptide Science 273 274 .
S. Zhang & J.P. Lee. (2008) Selectively 2 H‐labeledGlu/Asp: application to pK a measurements in Aβ amyloid peptides . The Journal of Peptide Research 55:1, pages 1-6.
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André Malanda Kimbonguila, Ahmed Merzouk, François Guibé & Albert Loffet. (1999) Allylic protection of thiols and cysteine: I: The allyloxycarbonylaminomethyl group. Tetrahedron 55:22, pages 6931-6944.
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François Guibé. (1998) Allylic protecting groups and their use in a complex environment part II: Allylic protecting groups and their removal through catalytic palladium π-allyl methodology. Tetrahedron 54:13, pages 2967-3042.
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Drew S. Poché, Stefan J. Thibodeaux, Victor C. Rucker, Isiah M. Warner & William H. Daly. (1997) Synthesis of Novel γ-Alkenyl l -Glutamate Derivatives Containing a Terminal C−C Double Bond To Produce Polypeptides with Pendent Unsaturation . Macromolecules 30:25, pages 8081-8084.
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Kerri L. Webster, Trevor J. Rutherford & David Gani. (1997) Comparison of solution-phase and solid-phase syntheses of a restrained proline-containing analogue of the nodularin macrocycle. Tetrahedron Letters 38:32, pages 5713-5716.
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Peter Wipf, April Cunningham, Robert L. Rice & John S. Lazo. (1997) Combinatorial synthesis and biological evaluation of Library of small-molecule Ser/Thr-protein phosphatase inhibitors. Bioorganic & Medicinal Chemistry 5:1, pages 165-177.
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THOMAS HOEG‐JENSEN, ARNO F. SPATOLA & ARNE HOLM. (2009) Amino monothio acids in solid‐phase synthesis of peptide thioamides. International Journal of Peptide and Protein Research 47:3, pages 190-200.
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André Malanda Kimbonguila, Ahmed Merzouk, François Guibé & Albert Loffet. (1994) The allyloxycarbonylaminomethyl group: a new allytic protection for the thiol group of cysteine. Tetrahedron Letters 35:48, pages 9035-9038.
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A. LOFFET & H.X. ZHANG. (2009) Allyl‐based groups for side‐chain protection of amino‐acids. International Journal of Peptide and Protein Research 42:4, pages 346-351.
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Claudio J. Salomon, Ernesto G. Mata & Oreste A. Mascaretti. (1993) Recent developments in chemical deprotection of ester functional groups. Tetrahedron 49:18, pages 3691-3734.
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Cynthia G. Fields, Albert Loffet, Steven A. Kates & Gregg B. Fields. (1992) The development of high-performance liquid chromatographic analysis of allyl and allyloxycarbonyl side-chain-protected phenylthiohydantoin amino acids. Analytical Biochemistry 203:2, pages 245-251.
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P. J. BELSHAW, S. MZENGEZA & G. A. LAJOIE. (2010) ChemInform Abstract: Chlorotrimethylsilane-Mediated Formation of ω-Allyl Esters of Aspartic and Glutamic Acids.. ChemInform 22:15, pages no-no.
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