Amide bond formation using amino acid fluorides

Lippert, John W.

doi:10.3998/ark.5550190.0006.e11

Arkivoc

2005

DOI: 10.3998/ark.5550190.0006.e11

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Amide bond formation using amino acid fluorides

John W. Lippert¹

Abstract: Amino acid fluorides have been used extensively in peptide synthesis. The following review surveys the formation and coupling of amino acid fluorides in both peptide and organic synthesis.

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Cited by 3 publications

References 11 publications

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Metal‐Free Aerobic Oxidative C−C Bond Cleavage between the Carbonyl Carbon and the α‐Carbon of α‐Azido Ketones: A Novel Synthesis of N‐Alkylated Benzamides

et al. 2017

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An unprecedented metal‐free approach has been achieved for the synthesis of N‐alkylated benzamides from phenacyl azides by oxidative cleavage of a C−C bond and formation of a new C−N bond in the presence of K2CO3. Various substituted phenacyl azides could be readily cleaved to access a variety of N‐alkylated benzamides by using the new protocol, which is a viable alternative for the construction of amide bonds. This metal‐free reaction forms amides in excellent yields with minimal generation of waste. The high functional group tolerance and diverse substrate scope make this reaction useful for organic synthesis.

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Metal‐Free Aerobic Oxidative C−C Bond Cleavage between the Carbonyl Carbon and the α‐Carbon of α‐Azido Ketones: A Novel Synthesis of N‐Alkylated Benzamides

et al. 2017

View full text Add to dashboard Cite

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Understandings on the Origin of Sands by Elementary School, Lower Secondary School, and University Students, and Problems on the Lesson of Rock Weathering

Hiroki

Yamasaki

Hirata

2011

Journal of Research in Science Education

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Clinical Analysis of Hyposmia-associated Taste Dysfunction

Kitano

Kobayashi²,

Imanishi³

et al. 2009

Nippon Jibiinkoka Gakkai Kaiho

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We clarified the clinical features of "flavor dysfunction," defined as olfactory dysfunction with self-reported hypogeusia but normal taste function in gustatory tests compared to those of "smell and taste dysfunction" hyposmia and hypogeusia in olfactory and gustatory tests. Patients with flavor dysfunction reported significantly milder taste loss than those with other smell and taste dysfunction. The major smell and taste loss etiology was upper respiratory tract infection (URI) in the flavor dysfunction group and the URI rate was significantly higher in the flavor dysfunction group than in the smell and taste dysfunction group. Smell identification thresholds in T & T olfactometry were not different between groups. Flavor dysfunction, hyposmia was treated medically but not with conventional hypogeusia medication. Medication including zinc was administered for other smell and taste dysfunction. Both groups significantly recovered from taste dysfunction. Our results indicate that treating olfactory dysfunction effectively improves flavor dysfunction but hypogeusia need not necessarily be treated. Hyposmia and hypogeusia must be treated together for other smell and taste dysfunction, making it vital that we conduct appropriate gustatory testing to correctly differentiate between flavor and other smell and taste dysfunctions.

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Amide bond formation using amino acid fluorides

Abstract: Amino acid fluorides have been used extensively in peptide synthesis. The following review surveys the formation and coupling of amino acid fluorides in both peptide and organic synthesis.

Cited by 3 publications

References 11 publications

Metal‐Free Aerobic Oxidative C−C Bond Cleavage between the Carbonyl Carbon and the α‐Carbon of α‐Azido Ketones: A Novel Synthesis of N‐Alkylated Benzamides

Metal‐Free Aerobic Oxidative C−C Bond Cleavage between the Carbonyl Carbon and the α‐Carbon of α‐Azido Ketones: A Novel Synthesis of N‐Alkylated Benzamides

Understandings on the Origin of Sands by Elementary School, Lower Secondary School, and University Students, and Problems on the Lesson of Rock Weathering

Clinical Analysis of Hyposmia-associated Taste Dysfunction

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