2-Mercaptopyridine-1-oxide-based peptide coupling reagents

Alberício, Fernando; Bailen, Miguel A.; Chinchílla, Rafael; Dodsworth, David J.; Nájera, Carmén

doi:10.1016/s0040-4020(01)00985-1

Cited by 39 publications

(27 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The choice of the particular series of heterocycle carbamates 7-12 was based on (i) the fact that analogous activated amino acids are specific substrates for peptide synthesis, 27 and (ii) the ease of synthesis of these carbamates from commercially available starting materials.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Aminolysis of N,N-Diethyl Carbamic Ester of HOBt Derivatives

Khattab¹,

Hassan²,

Hamed³

et al. 2010

Bulletin of the Korean Chemical Society

Self Cite

View full text Add to dashboard Cite

The reaction of N,N-diethyl carbamates of 1H- [1,2,3]triazolo [4,5-b]pyridin-1-ol (4-HOAt) 7, 3H-[1,2,3]triazolo [4,5-b] and 6-nitro-1H-benzo[d][1,2,3]triazol-1-ol (NO2-HOBt) 12 with morpholine and piperidine in CH3CN underwent acyl nucleophilic substitution to give the corresponding carboxamide derivatives. The reactants and products were identified by elemental analysis, IR and NMR. We measured the kinetics of these reactions spectrophotometrically in CH3CN at a range of temperatures. The rates of morpholinolysis and piperidinolysis were found to fit the Hammett equation and correlated with σ-Hammett values. The values were 1.44 -1.21 for morpholinolysis and 1.95 -1.72 for piperidinolysis depending on the temperature. The Brønsted-type plot was linear with a βlg = −0.49 ± 0.02 and −0.67 ± 0.03. The kinetic data and structure-reactivity relationships indicate that the reaction of 9-12 with amines proceeds by a concerted mechanism. The deviation from linearity of the correlation ∆H # vs. ∆S # and plot of logkpip vs. logkmorph and Brønsted-type correlation indicate that the reactions of amines with carbamates 7 and 8 is attributed to the electronic nature of their leaving groups.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis and Aminolysis of N,N-Diethyl Carbamic Ester of HOBt Derivatives

Khattab¹,

Hassan²,

Hamed³

et al. 2010

Bulletin of the Korean Chemical Society

Self Cite

View full text Add to dashboard Cite

show abstract

“…[11][12][13][14][15] Some of these reagents are now available on polymer supports for ease of use in parallel synthesis and diversity investigations. 15 Macrolactamization, not surprisingly, is often the method of choice for peptidomimetic macrocycles and has been successfully employed for a wide range of structures from the small ring inhibitors (5) of neutral endopeptidase 24.11 (NEP) 16,17 (Figure 11.1, ring closure site indicated with reagent used for cyclization (HATU (2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate), FDPP (pentafluorophenyl diphenylphosphinate), TCBC (2,4,6-trichlorobenzoyl chloride, Yamaguchi's reagent)) to the larger macrocycles (6) pioneered by Robinson as protein epitope mimics (PEM).…”

Section: Macrolactamization and Macrolactonizationmentioning

confidence: 99%

The Synthesis of Macrocycles for Drug Discovery

Peterson¹

2014

Macrocycles in Drug Discovery

View full text Add to dashboard Cite

Despite the attractive nature of macrocyclic compounds for use in new pharmaceutical discovery, applications have been hindered due to the lack of appropriate synthetic methods, in particular for the construction of libraries of such molecules. However, over the last decade, a number of effective and versatile methodologies suitable for macrocyclic scaffolds have been developed and applied successfully. These include classical coupling and substitution reactions, ring-closing metathesis (RCM), cycloaddition (“click”) chemistry, multicomponent reactions (MCR), numerous organometallic-mediated processes and others. This chapter presents a comprehensive compilation of these strategies and provides examples of their use in drug discovery, along with a description of those approaches that have proven effective for the assembly of macrocyclic libraries suitable for screening.

show abstract

“…1 H-NMR (CDCl 3 ): δ = 3.85 (s, 3H, OCH 3 ); 4.00 (s, 6H, OCH 3 ); 6.99 (d, 2H, J = 7.5 Hz, C 6 H 4 -); 8.09 (d,2H,J = 7.5 Hz, [ppm].…”

Section: 17mentioning

confidence: 99%

P-Triazinylphosphonium chlorides as a new group of coupling reagents

et al. 2013

View full text Add to dashboard Cite

Abstract:© Versita Sp. z o.o. Keywords: P-triazinylphosphonium chlorides • Dealkylation Research ArticleTertiary phosphines in reaction with 2-chloro-4,6-dialkoxy-1,3,5-triazines gave unstable quaternary P-triazinylphosphonium chlorides, which readily decomposed with a departure of the alkyl group of the triazine ring substituent. Stable quaternary P-triazinylphosphonium chlorides were obtained only in reaction of 2-chloro-4,6-diphenoxy-1,3,5-triazine. Both, stable quaternary P-triazinylphosphonium chlorides as well unstable analogues prepared in situ activated carboxylic acid yielding "superactive" triazine esters, useful as highly efficient reagents in peptide bond synthesis.

show abstract

2-Mercaptopyridine-1-oxide-based peptide coupling reagents

Cited by 39 publications

References 40 publications

Synthesis and Aminolysis of N,N-Diethyl Carbamic Ester of HOBt Derivatives

Synthesis and Aminolysis of N,N-Diethyl Carbamic Ester of HOBt Derivatives

The Synthesis of Macrocycles for Drug Discovery

P-Triazinylphosphonium chlorides as a new group of coupling reagents

Contact Info

Product

Resources

About