Peptidsynthesen mit gemischten Anhydriden aus <i>N</i>‐Acyl‐aminosäuren und Saccharin

Micheel, Fritz; Lorenz, Manfred

doi:10.1002/jlac.19666980128

Cited by 7 publications

(2 citation statements)

References 24 publications

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“…Additionally, a heterocyclic-substituted carboxylic acid ( 5d ) and α,β-unsaturated carboxylic acid ( 5f ) also gave the corresponding N -acylsaccharins. Aliphatic carboxylic acids and the protected amino acid N -Cbz glycine also afforded the corresponding N -acylsaccharins in moderate to good yields. Other protected amino acids with α-substituents (Boc-Val-OH and Boc-Ala-OH) gave very low product conversion presumably because of steric hindrance at the α-positions.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of N-Hydroxysuccinimide Esters, N-Acylsaccharins, and Activated Esters from Carboxylic Acids Using I₂/PPh₃

Handore,

Lu,

Park

et al. 2024

J. Org. Chem.

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A method for the syntheses of isolable, active esters is described in which carboxylic acids are treated with triphenylphosphine, iodine, and triethylamine. Active esters accessible in this way include N-hydroxysuccinimide esters, Nhydroxyphthalimide esters (N-(acyloxy)phthalimides), N-acylsaccharins, pentafluorophenol esters, pentachlorophenol esters, Nhydroxybenzotriazole esters, and hexafluoro-2-propanol esters. The approach can be similarly applied toward the formation of Nacylsaccharins and N-acylimidazoles. The method is suitable for the formation of isolable active esters of aromatic and aliphatic activated acids as well as α-amino acid derivatives. These products are widely used reagents in organic synthesis, peptide synthesis, medicinal chemistry, and chemical biology (e.g., for bioconjugations). The method has broad substrate scope, uses simple and inexpensive reagents, avoids the use of carbodiimides or other coupling agents, and occurs at room temperature. Additionally, the diastereomers of compound Boc-Ala−NHCHPh are demonstrated to be distinguishable by 1 H NMR (in DMSO-d 6 ), allowing for a straightforward NMR method to establish the degree of racemization of activated esters of Boc-Ala or amide bond formations using Boc-Ala.

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Section: Resultsmentioning

confidence: 99%

Synthesis of N-Hydroxysuccinimide Esters, N-Acylsaccharins, and Activated Esters from Carboxylic Acids Using I₂/PPh₃

Handore,

Lu,

Park

et al. 2024

J. Org. Chem.

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“…All these factors are responsible for the low yields of peptides 134 . A novel application of saccharin is its use in the synthesis of mixed anhydrides with acylaminoacids 135 :…”

Section: Rcoo + Clb(och3)a -* Rcoob (Och3)2 Rconhr'mentioning

confidence: 99%

Methods of Synthesis of Peptides

Mitin¹,

Zapevalova²

1977

Russ. Chem. Rev.

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Die Addition von Imidazolderivaten an DCCI; eine Nebenreaktion bei der Synthese von Histidinpeptiden

Rink

Riniker

1974

Helvetica Chimica Acta

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91-92 831 benzoate of 7 solvolyzes faster than the anti-7-norbornenyl-p-nitrobenzoate, by a factor of 103, is attributed to a participation of the second double bond during solvolysis [13].In accordance with this view we found, by minimizing the energy as a function of the geometry [14] of 7 and its cation 8, that not only the distance between the formal positive center and the adjacent double bond is shortened (0.40 A) but also the distance between the two double bonds (0.11 A). All other bond lengths in the cation were found to be the same as the corresponding ones in 7.We appreciate very much the helpful discussion with Prof. R. Hoffmann, Cornell University.

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Peptidsynthesen mit gemischten Anhydriden aus N‐Acyl‐aminosäuren und Saccharin

Cited by 7 publications

References 24 publications

Synthesis of N-Hydroxysuccinimide Esters, N-Acylsaccharins, and Activated Esters from Carboxylic Acids Using I₂/PPh₃

Synthesis of N-Hydroxysuccinimide Esters, N-Acylsaccharins, and Activated Esters from Carboxylic Acids Using I₂/PPh₃

Methods of Synthesis of Peptides

Die Addition von Imidazolderivaten an DCCI; eine Nebenreaktion bei der Synthese von Histidinpeptiden

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Peptidsynthesen mit gemischten Anhydriden aus N‐Acyl‐aminosäuren und Saccharin

Cited by 7 publications

References 24 publications

Synthesis of N-Hydroxysuccinimide Esters, N-Acylsaccharins, and Activated Esters from Carboxylic Acids Using I2/PPh3

Synthesis of N-Hydroxysuccinimide Esters, N-Acylsaccharins, and Activated Esters from Carboxylic Acids Using I2/PPh3

Methods of Synthesis of Peptides

Die Addition von Imidazolderivaten an DCCI; eine Nebenreaktion bei der Synthese von Histidinpeptiden

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Product

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Synthesis of N-Hydroxysuccinimide Esters, N-Acylsaccharins, and Activated Esters from Carboxylic Acids Using I₂/PPh₃

Synthesis of N-Hydroxysuccinimide Esters, N-Acylsaccharins, and Activated Esters from Carboxylic Acids Using I₂/PPh₃