An Efficient Synthesis of N-Protected β-Aminoethanesulfonyl Chlorides: Versatile Building Blocks for the Synthesis of Oligopeptidosulfonamides

Brouwer, Arwin J.; Monnee, Menno C. F.; Liskamp, Rob M. J.

doi:10.1055/s-2000-7615

Cited by 43 publications

(57 citation statements)

References 7 publications

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“…From Tables 3 and 4 we see that the ESI-MS analysis exhibits an interesting distribution of multiply charged ions of A␤ [17][18][19][20][21] and A␤ [25][26][27][28][29][30][31][32][33][34][35] fragments and their complexes with BSBps in various stoichiometric combinations. In particular, the intensity of the observed peaks, corresponding to the various complexes formed by A␤ fragments bound to BSBps (data not shown), indicate that Ac-LPFFN-NH 2 binds more strongly than Ac-LPFFD-NH 2 and Tau-LPFFD-NH 2 .…”

Section: Resultsmentioning

confidence: 99%

“…On the basis of these findings and with the aim of identifying which region of the A␤ interacts with the ligand, we have studied the non-covalent interactions of Ac-LPFFD-NH 2 and of its two derivatives, Ac-LPFFN-NH 2 and Tau-LPFFD-NH 2 , with the two peptide fragments, A␤ [25][26][27][28][29][30][31][32][33][34][35] and A␤ [17][18][19][20][21] .…”

Section: Resultsmentioning

confidence: 99%

“…where a-b stands for the [25][26][27][28][29][30][31][32][33][34][35] (Table 3) or 17-21 (Table 4) fragment, and BSBp j,j ϭ 1, 2, and 3, are the three BSBps considered in this paper. The percentage of bound amyloid, given in the fifth column of the Tables 3 and 4, was computed as the ratio of the concentration of (single or pairs of) A␤ a-b fragments, bound with one or two BSBps with respect to the total A␤ a-b concentration.…”

Section: Resultsmentioning

confidence: 99%

“…The peptides were characterized on a Q-TOF MICRO spectrometer (Micromass, now Waters, Manchester, UK) equipped with an ESI source, in the positive ion mode, and data were analyzed using the MassLynx software (Waters). In Table 2 we compared the theoretical expected numbers with the values of m/z for the [MϩH] ϩ molecular ions associated to the A␤ [17][18][19][20][21] , A␤ [25][26][27][28][29][30][31][32][33][34][35] , Ac-LPFFD-NH 2 , Tau-LPFFD-NH 2 , and Ac-LPFFN-NH 2 peptides.…”

Section: Experimental Methodsmentioning

confidence: 99%

“…The A␤ [17][18][19][20][21] and A␤ [25][26][27][28][29][30][31][32][33][34][35] (34) and coupled to the resin-bound protected pentapeptide in dichloromethane in the presence of 4-methylmorpholine (7 eq). The coupling mixture was shaken overnight.…”

Section: Experimental Methodsmentioning

confidence: 99%

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Computational and Experimental Studies on β-Sheet Breakers Targeting Aβ1–40 Fibrils

Minicozzi

Chiaraluce

Consalvi

et al. 2014

Journal of Biological Chemistry

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Background: ␤-Amyloid aggregates are at the basis of Alzheimer disease development. Short synthetic peptides are seen to inhibit polymerization. Results: Various synthetic peptides have been studied by MD simulations and tested experimentally. Conclusion:Combined results indicate Ac-LPFFN-NH 2 as an effective lead compound able to slow down A␤ 1-40 aggregation. Significance: Designing potential A␤ aggregation inhibitors will help fight Alzheimer disease.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Experimental Methodsmentioning

confidence: 99%

Section: Experimental Methodsmentioning

confidence: 99%

See 3 more Smart Citations

Computational and Experimental Studies on β-Sheet Breakers Targeting Aβ1–40 Fibrils

Minicozzi

Chiaraluce

Consalvi

et al. 2014

Journal of Biological Chemistry

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Preparation of Alkanesulfonyl Chlorides from S ‐Alkyl Isothiourea Salts via N ‐Chlorosuccinimide Mediated Oxidative Chlorosulfonation

Yang¹,

2014

Organic Syntheses

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Synthesis of a Six-Membered-Ring (2R)-10a-Homobornane-10a,2-sultam and Structural Comparison with Oppolzer's, Lang's, and King's Sultams

Piątek¹,

Chapuis²,

Jurczak³

2002

HCA

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The new six-membered-ring (2R)-10a-homobornane-10a,2-sultam (À)-3a was synthesized and its X-ray structural analysis was compared with that of the novel structure of the five-membered-ring (2R)-bornane-10,2sultam analogues (À)-1a,b as well as with that already published for the six-membered-ring trans-decalin-like sultam 4a. Based on DN** density-function calculations and X-ray crystallographic studies of the N-methylated analogues (À)-1e and 4b and by comparing with the conformation of the N-fluoro derivatives (À)-1c and ()-1d, the anomeric stabilization was estimated to be smaller than the 2.0 ± 2.5 kcal/mol earlier suggested. The direction of pyramidalization is rationalized in terms of H-bond and steric and electronic interactions and extended to the known toluenesultam derivatives 10a ± c. 2 ) For N lp through-bond and through-space directing interactions, initially suggested by M¸ller and Eschenmoser, see [10a]. For nonexhaustive more recent examples, see [10b ± g]. Cieplak also proposed a hyperconjugative influence of the N lp on the incipient bond-formation through the intermediacy of a sp 2 atom, see Schemes 85 and 86 as well as reference 105 in [11]. More recently, King et al. also suggested an anomeric stabilization [12a]. We now wish to report the synthesis of the tricyclic six-membered-ring sultam (À)-3a as well as its X-ray-structural analysis for comparison with those of (À)-1a,b,e and the racemic six-membered-ring trans-decalin-like sultams 4a,b [12a].Results. ± The commercially available ()-camphorsulfonyl chloride 5 was treated with CH 2 N 2 in Et 2 O to afford, after thermal treatment, the known unsaturated C 11 ketone ()-6 in 84% yield according to a previously reported procedure [13]. Further protection of the carbonyl moiety (ethylene glycol, TsOH, THF; 79% yield) followed by hydroboration (9-BBN, THF, 208, then NaOH, H 2 O 2 ; 90% yield) furnished the known primary alcohol (À)-7a [14] 3 ). This intermediate was then converted to the corresponding crude unreported mesylate (À)-7b (MsCl, CH 2 Cl 2 , Et 3 N, 08; 95% yield [16]) prior to an S N 2 displacement (AcSK, DMSO, 458; 96% yield [17]) to afford the thioacetate (À)-7c. Oxidation (30% H 2 O 2 solution, 85%, AcOH solution [18]), with concomitant deprotection, delivered the new sulfonic acid ()-8a in 92% isolated yield. A route similar to that earlier published by Oppolzer et al.[1] was then followed for the preparation of (À)-3a.Thus, treatment with SOCl 2 at 1008 [19] furnished the sulfonyl chloride (À)-8b in 63% yield 4 ). Rather than addition of gaseous NH 3 under anhydrous conditions [21], we preferred, for technical reasons, the NH 4 OH procedure initially reported by Sutherland and co-workers [22] and recently re-actualized by Davis et al. [19] and Capet et al. [23]. The new sulfonamide ()-8c, thus obtained in 69% yield, was then cyclized under basic conditions (NaOMe, MeOH [1]) to furnish the sulfonimine (À)-9 in 75% yield 5 ).Helvetica Chimica Acta ± Vol. 85 (2002) 1974 3 ) According to [15], a lower chemical yield was obtaine...

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An Efficient Synthesis of N-Protected β-Aminoethanesulfonyl Chlorides: Versatile Building Blocks for the Synthesis of Oligopeptidosulfonamides

Abstract: A very efficient method for the synthesis of b-aminoethanesulfonyl chlorides is described. These aliphatic functionalized sulfonyl chlorides are accessible starting from a variety of protected amino acids, including those having functionalized side chains.

Cited by 43 publications

References 7 publications

Computational and Experimental Studies on β-Sheet Breakers Targeting Aβ1–40 Fibrils

Computational and Experimental Studies on β-Sheet Breakers Targeting Aβ1–40 Fibrils

Preparation of Alkanesulfonyl Chlorides from S ‐Alkyl Isothiourea Salts via N ‐Chlorosuccinimide Mediated Oxidative Chlorosulfonation

Synthesis of a Six-Membered-Ring (2R)-10a-Homobornane-10a,2-sultam and Structural Comparison with Oppolzer's, Lang's, and King's Sultams

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