Solid-phase synthesis of peptidyl thioacids employing a 9-fluorenylmethyl thioester-based linker in conjunction with Boc chemistry
(Chemical Equation Presented) A method for the synthesis of peptidyl thioacids is described on the basis of the use of the N-[9-(thiomethyl)-9H- fluoren-2-yl]succinamic acid and cross-linked aminomethyl polystyrene resin. The method employs standard Boc chemistry SPPS techniques in conjunction with 9-fluorenylmethyloxycarbonyl protection of side-chain alcohols and amines and 9-fluorenylmethyl protection of side-chain acids and thiols. Cleavage from the resin is accomplished with piperidine, which also serves to remove the side-chain protection and avoids the HF conditions usually associated with the resin cleavage stage of Boc chemistry SPPS. The so-obtained thioacids are converted to simple thioesters in high yield by standard alkylation according to well-established methods. 2009 American Chemical Society.
Crich, David,Sana, Kasinath
scheme or table
p. 7383 - 7388
(2010/01/16)
Single step syntheses of ω-9-fluorenylmethyl esters of aspartic and glutamic acids
Base lability of the 9-fluorenylmethyl ester makes this group useful in solid phase peptide synthesis when used in combination with the tBoc methodology for preparing cyclic peptides. We describe a simple one step synthesis of the 9-fluorenylmethyl esters of aspartic and glutamic acids.
Belshaw,Adamson,Lajoie
p. 1001 - 1005
(2007/10/02)
Convenient Syntheses of Fluorenylmethyl-Based Side Chain Derivatives of Glutamic and Aspartic acids, Lysine and Cysteine
Efficient and practical one-pot syntheses of the fluorenylmethyl-based side chain derivatives of glutamic and aspartic acids, lysine, and cysteine are described.Likewise, stability/lability of these derivatives towards solvents and reagents used in solid
Albericio, F.,Nicolas, E.,Rizo, J.,Ruiz-Gayo, M.,Pedroso, E.,Giralt, E.
p. 119 - 122
(2007/10/02)
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