The Synthesis of N-(2-Benzyl-4-Δ<sup>2</sup>-oxazolinoyl)-valine<sup>1</sup>

Adkins, Homer; Ross, Robert M.; Schroeder, D. C.; Mahoney, C. L.; Gilbert, Walter

doi:10.1021/ja01630a040

Cited by 12 publications

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“…Cbz-Ser-anilide (10). 27 Compound 10 was synthesized as described for 9 using Cbz-Ser-OH 7 (108 mg, 0.45 mmol, 1 equiv) and obtained in 93% yield as a solid (423 mg).…”

Section: Methodsmentioning

confidence: 99%

Enzymatic Synthesis ofC-Terminal Arylamides of Amino Acids and Peptides

et al. 2009

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A mild and cost-efficient chemo-enzymatic method for the synthesis of C-terminal arylamides of amino acid and peptides is described. Using the industrial serine protease Alcalase under near-anhydrous conditions, C-terminal arylamides of N-Cbz-protected amino acids and peptides could be obtained from the corresponding C-terminal carboxylic acids, methyl (Me) or benzyl (Bn) esters, in high chemical and enantio- and diastereomeric purities. Yields ranged between 50% and 95% depending on the size of the aryl substituents and the presence of electron-withdrawing substituents. Complete alpha-C-terminal selectivity could be obtained even in the presence of various unprotected side-chain functionalities such as beta/gamma-carboxyl, hydroxyl, and guanidino groups. In addition, the use of the cysteine protease papain and the lipase Cal-B gave anilides in high yields. The chemo-enzymatic synthesis of arylamides proved to be completely free of racemization, in contrast to the state-of-the-art chemical methods.

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“…Cbz-Ser-anilide (10). 27 Compound 10 was synthesized as described for 9 using Cbz-Ser-OH 7 (108 mg, 0.45 mmol, 1 equiv) and obtained in 93% yield as a solid (423 mg).…”

Section: Methodsmentioning

confidence: 99%

Enzymatic Synthesis ofC-Terminal Arylamides of Amino Acids and Peptides

et al. 2009

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Oxazoles

Turchi¹

1986

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Beiträge zur Peptidsynthese, IV. Darstellung und peptidsynthetische Verwendung von O‐Benzyl‐serin

Gräßmann¹,

Wünsch²,

Deufel³

et al. 1958

Chem. Ber.

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Es wird die Synthese von 0-Benzyl-DL-serin aus Acrylester beschrieben. Die 0-maskierte Aminosaure laBt sich durch katalytische Hydrierung leicht in reines DL-Serin uberfuhren und zur Synthese von Peptiden des Serins verwenden. Die Synthese von Peptiden der Hydroxyaminosauren ist neben einigen unwesentlichen Versuchen3-5) den letzten 15 Jahren vorbehalten geblieben. 1942 konnten J. s. F R u T O N~) und wenig spater E. L. SMTH und M. BERGMANN~) zeigen, daD auchCarbobenzoxy-serin bzw. -hydroxyprolin nach der Azidmethode unter Einhaltung tiefer Temperaturen mit Aminosaureestern zum Carbobenzoxy-peptidester gekuppelt werden konnen. Serin-peptide sind in der Folgezeit ohne besonderen Schutz der Hydroxylgruppe nach diesem Verfahrens-13) sowie nach der gemischten Anhydridund Carbodiimidmethodel4.15) mehrfach dargestellt worden (zur Synthese von Hydroxyprolyl-peptiden siehe E. WUNSCH~~)).Fur die Verwendung der Fischerschen Saurechlorid-bzw. der Goldschmidtschen Phosphorazomethode zur Synthese von Peptiden des Typus ,,Hydroxyaminosaure-X" war jedoch eine Maskierung der alkoholischen Hydroxylgruppe unerlaDlich. Als erste Moglichkeit bot sich die Veresterung zu Acyloxy-aminosauren17-20). M. FRANKEL 1) P. DEUFEL, Diplomarbeit, Univ. Munchen 1955; A. ZWICK, Diplomarbeit, Univ.

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The Synthesis of N-(2-Benzyl-4-Δ²-oxazolinoyl)-valine¹

Cited by 12 publications

References 0 publications

Enzymatic Synthesis ofC-Terminal Arylamides of Amino Acids and Peptides

Enzymatic Synthesis ofC-Terminal Arylamides of Amino Acids and Peptides

Oxazoles

Beiträge zur Peptidsynthese, IV. Darstellung und peptidsynthetische Verwendung von O‐Benzyl‐serin

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The Synthesis of N-(2-Benzyl-4-Δ2-oxazolinoyl)-valine1

Cited by 12 publications

References 0 publications

Enzymatic Synthesis ofC-Terminal Arylamides of Amino Acids and Peptides

Enzymatic Synthesis ofC-Terminal Arylamides of Amino Acids and Peptides

Oxazoles

Beiträge zur Peptidsynthese, IV. Darstellung und peptidsynthetische Verwendung von O‐Benzyl‐serin

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The Synthesis of N-(2-Benzyl-4-Δ²-oxazolinoyl)-valine¹