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DOI: 10.1055/s-0028-1088211
Utilization of N,N,N′,N′-Tetramethylfluoroformamidinium Hexafluorophosphate (TFFH) in Peptide and Organic Synthesis
Publication History
Publication Date:
16 March 2009 (online)
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Abstract
N,N,N′,N′-Tetramethylfluoroformamidinium hexafluorophosphate (TFFH) has been shown to be an excellent peptide-coupling reagent. It is an easily handled, crystalline compound, it has a long shelf life, and it reacts rapidly with carboxylic acids to give the corresponding acid fluorides or mixed anhydrides depending on the reaction conditions. TFFH has been shown to be useful as a peptide-coupling reagent and for the preparation of various carboxylic acid derivatives. Both aspects will be surveyed in this Account.
1 Introduction
2 Formation of Carboxylic Acid Halides
3 General Method for the Synthesis of Fluoroformamidinium Salts
4 Solution and Solid-Phase Peptide Coupling Using TFFH
5 Synthesis of Small Phosphotyrosine-Containing Peptides and Peptide Mimetics Incorporating α-Methylated Amino Acids
6 Synthesis of Lysine Analogues
7 Synthesis of Proline Conformation in Tripeptide Fragments of Bovine Pancreatic Ribonuclease A Containing the Nonnatural Proline Analogue 5,5-Dimethylproline
8 Synthesis of Different Types of Dipeptide Building Units Containing N- or C-Terminal Arginine for the Assembly of Backbone Cyclic Peptides
9 Synthesis of Peptidyl Methylcoumarin Esters as Substrates and Active-Site Titrants for Prohormone Processing
10 Synthesis of Boc-(N-All)Xaa-(N-All)Xaa-OMe
11 Synthesis of Alamethicin F30 and Analogues Using TFFH
11.1 C-Terminal Alamethicin F30-Fullerene C60 and C70 Conjugates
11.2 N-Terminal Alamethicin F30-Fullerene C60 Conjugate
12 Miscellaneous Examples
12.1 Synthesis of Isothiocyanates and Hydrazides
12.2 Conversion of Carboxylic Acids into Anilides and Azides
12.3 Acylation of Alcohols, Thiols, and Dithiocarbamates
12.4 Conversion of Carboxylic Acids into Alcohols and Hydroxamic Acids Using TFFH/PTF
12.5 Preparation of 2-Aminobenzimidazole, 2-Aminobenzoxazole, and 2-Aminobenzothiazole Derivatives
12.6 Formation of Interchain Carboxylic Anhydrides on Self-Assembled Monolayers
12.7 Synthesis of the A1B(A)C Fragment of Everninomicin 13,384-1
12.8 Synthesis of Chiral Polyionic Dendrimers with Complementary Charges
13 Conclusion
Key words
TFFH - amino acid fluorides - solution-phase peptide synthesis - solid-phase peptide synthesis - carboxylic acid derivatives - heterocycles
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