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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 11, 1981 - Issue 4
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Original Articles

Improved Syntheses of Nε-Tert-butyloxycarbonyl-L-lysine and Nα-Benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-I-lysine

John W. Scott Chemical Research Deparment, Hoffmann-La Roche Inc., Nutley, New Jersey, 07110
,
David Parker Chemical Research Deparment, Hoffmann-La Roche Inc., Nutley, New Jersey, 07110
&
David R. Parrish Chemical Research Deparment, Hoffmann-La Roche Inc., Nutley, New Jersey, 07110
Pages 303-314 | Published online: 05 Dec 2006

Citations (35)

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Ełżbieta Masiukiewicz, Stanislaw Wiejak & Barbara Rzeszotarska. (1999) AN IMPROVED SYNTHESIS OF N α-BENZYLOXYCARBONYL-L-LYSINE. Organic Preparations and Procedures International 31:4, pages 456-459.
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Elzbieta Masiukiewicz, Barbara Rzeszotarska & Jaroslaw Szczerbaniewicz. (1992) A ONE-POT SYNTHESIS OF N αBENZYLOXYCARBONYL N ω-t-BUTOXYCARBONYL-L-ORNITHINE AND L-LYSINE. Organic Preparations and Procedures International 24:2, pages 191-194.
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EdgarP. Heimer, Ching-Tso Wang, TheodoreJ. Lambros & ArthurM. Felix. (1983) DIRECT SYNTHESIS OF Nα-BENZYLOXYCARBONYL-Nε-t-BUTYLOXY-CARBONYL-L-LYSINE FROM L-LYSINE. Organic Preparations and Procedures International 15:6, pages 379-385.
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S.T. Chen & K.T. Wang. (1983) THE SYNTHESIS OF HIGH PURITY Nα-BENZYLOXYCARBONYL Nε-t-BUTYLOXYCARBONYL-L-LYSINE. Organic Preparations and Procedures International 15:5, pages 361-364.
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Articles from other publishers (31)

Asmaa Habib, José J. Garrido-González, Estela Sánchez-Santos, Irene Boya del Teso, Francisca Sanz, Victoria Alcázar, Ángel L. Fuentes de Arriba & Joaquín R. Morán. (2023) 5-Chloro-8-nitro-1-naphthoyl (NNap): A Selective Protective Group for Amines and Amino Acids. Organic Letters 25:22, pages 4103-4107.
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Alexander Amatuni, Anton Shuster, Daniel Abegg, Alexander Adibekian & Hans Renata. (2023) Comprehensive Structure–Activity Relationship Studies of Cepafungin Enabled by Biocatalytic C–H Oxidations. ACS Central Science.
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Alan Steven. 2022. Green Chemistry in Drug Discovery. Green Chemistry in Drug Discovery 327 372 .
Maré Cudic & Gregg B. Fields. (2020) Modulation of receptor binding to collagen by glycosylated 5‐hydroxylysine: Chemical biology approaches made feasible by Carpino's Fmoc group. Peptide Science 112:4.
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Ashley R. Wolf, Darryl A. Wesener, Jiye Cheng, Alexandra N. Houston-Ludlam, Zachary W. Beller, Matthew C. Hibberd, Richard J. Giannone, Samantha L. Peters, Robert L. Hettich, Semen A. Leyn, Dmitry A. Rodionov, Andrei L. Osterman & Jeffrey I. Gordon. (2019) Bioremediation of a Common Product of Food Processing by a Human Gut Bacterium. Cell Host & Microbe 26:4, pages 463-477.e8.
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Yi LiuGenguang JiaXin LingNuo LanYouguang ZhengSai LiLing ZhangLing LiuRongli ZhangYunsheng Xue. (2012) Decomposition of copper – amino acid complexes by oxalic acid dihydrate. Canadian Journal of Chemistry 90:6, pages 557-559.
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Jan Romanski, Marcin Karbarz, Krystyna Pyrzynska, Janusz Jurczak & Zbigniew Stojek. (2011) Polymeric hydrogels modified with ornithine and lysine: Sorption and release of metal cations and amino acids. Journal of Polymer Science Part A: Polymer Chemistry 50:3, pages 542-550.
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Vommina V. Sureshbabu & Narasimhamurthy Narendra. 2011. Amino Acids, Peptides and Proteins in Organic Chemistry. Amino Acids, Peptides and Proteins in Organic Chemistry 1 97 .
Fabio Bellina & Renzo Rossi. (2009) Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp 3 -Hybridized C−H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides . Chemical Reviews 110:2, pages 1082-1146.
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Satendra S. Chauhan. (2009) Enantioselective synthesis of (L)-Fmoc-α-Me-Lys(Boc)-OH via diastereoselective alkylation of oxazinone as a chiral auxiliary. Tetrahedron Letters 50:49, pages 6913-6915.
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Meirav Holmdahl, Stefan R. Ahlfors, Rikard Holmdahl & Christer Hansson. (2008) Structure-Immune Response Relationships of Hapten-Modified Collagen II Peptides in a T-Cell Model of Allergic Contact Dermatitis. Chemical Research in Toxicology 21:8, pages 1514-1523.
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Shaik Nowshuddin & A. Ram Reddy. (2006) Decomposition of copper–amino acid complexes by sodium sulfide. Tetrahedron Letters 47:29, pages 5159-5161.
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M. Cudic, J.L. Lauer-Fields & G. B. Fields. (2008) Improved synthesis of 5-hydroxylysine (Hyl) derivatives*. The Journal of Peptide Research 65:2, pages 272-283.
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Gummadi Sailaja, Shaik Nowshuddin & M.N.A. Rao. (2004) Sodium borohydride efficiently removes copper from amino acid–copper complexes. Tetrahedron Letters 45:50, pages 9297-9298.
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Wenlin Lee & Marvin J. Miller. (2004) Concise Synthesis of 4-Acylamino Analogues of 2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic Acids (LY354740) from an Acylnitroso Diels−Alder Cycloadduct. The Journal of Organic Chemistry 69:13, pages 4516-4519.
Crossref
Juan Rodríguez Hernández & Harm‐Anton Klok. (2003) Synthesis and ring‐opening (co)polymerization of L ‐lysine N ‐carboxyanhydrides containing labile side‐chain protective groups . Journal of Polymer Science Part A: Polymer Chemistry 41:9, pages 1167-1187.
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Oskar Keller, Walter E. Keller, Gert van Look & Gernot Wersin. 2003. Organic Syntheses. Organic Syntheses 160 160 .
So Ha Lee & Chan Seong Cheong. (2001) Selective reactions of reactive amino groups in polyamino compounds by metal-chelated or -mediated methods. Tetrahedron 57:23, pages 4801-4815.
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Michel Wakselman. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Paul Sampson. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Maciej Adamczyk, Donald D Johnson & Rajarathnam E Reddy. (2000) Bone collagen cross-links: an efficient one-pot synthesis of (+)-pyridinoline and (+)-dexoypyridinoline. Tetrahedron: Asymmetry 11:11, pages 2289-2298.
Crossref
Johan Broddefalk, Mattias Forsgren, Ingmar Sethson & Jan Kihlberg. (1999) Preparation of a Diglycosylated Hydroxylysine Building Block Used in Solid-Phase Synthesis of a Glycopeptide from Type II Collagen. The Journal of Organic Chemistry 64:24, pages 8948-8953.
Crossref
Hui Huang, Pavel Martasek, Linda J. Roman, Bettie Sue Siler Masters & Richard B. Silverman. (1999) N ω -Nitroarginine-Containing Dipeptide Amides. Potent and Highly Selective Inhibitors of Neuronal Nitric Oxide Synthase . Journal of Medicinal Chemistry 42:16, pages 3147-3153.
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Johan Broddefalk, Johan Bäcklund, Fredrik Almqvist, Martin Johansson, Rikard Holmdahl & Jan Kihlberg. (1998) T Cells Recognize a Glycopeptide Derived from Type II Collagen in a Model for Rheumatoid Arthritis. Journal of the American Chemical Society 120:31, pages 7676-7683.
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Jos� L. Espartero, Bernard Coutin & Hikaru Sekiguchi. (1993) Synthesis of a polyamide from l-aspartic acid and l-lysine. Polymer Bulletin 30:5, pages 495-500.
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G. Gallant, R. Salvador & H. Dulude. (2016) Synthesis, anti-HIV and anti-Proliferative Activity of New Urea and Nitrosourea Derivatives of Amino Acids. Antiviral Chemistry and Chemotherapy 2:5, pages 313-319.
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Marlyse Gander‐Coquoz & Dieter Seebach. (2004) Herstellung enantiomerenreiner, α‐alkylierter Lysin‐, Ornithin‐ und Tryptophan‐Derivate. Helvetica Chimica Acta 71:1, pages 224-236.
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Jack E. Baldwin, Stephen J. Killin, Robert M. Adlington & Udo Spiegel. (1988) Synthesis of n-benzyloxycarbonyl-l-α-aminoadipic acid, α-benzyl ester. Tetrahedron 44:9, pages 2633-2636.
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Shui-Tein Chen, Chih-Shyong Weng & Kung-Tsung Wang. (1987) The Synthesis of p -Methoxybenzyloxycarbonyl Amino Acids . Journal of the Chinese Chemical Society 34:2, pages 117-123.
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J. Meienhofer. 1985. Chemistry and Biochemistry of the Amino Acids. Chemistry and Biochemistry of the Amino Acids 297 337 .
J. W. SCOTT, D. PARKER & D. R. PARRISH. (2016) ChemInform Abstract: IMPROVED SYNTHESES OF Nε‐(TERT‐BUTYLOXYCARBONYL)‐L‐LYSINE AND Nα‐(BENZYLOXYCARBONYL)‐Nε‐(TERT‐BUTYLOXYCARBONYL)‐L‐LYSINE. Chemischer Informationsdienst 12:43.
Crossref

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