The chemistry of 5-oxazolones

Baltazzi, Evan

doi:10.1039/qr9550900150

Cited by 53 publications

(11 citation statements)

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“…1. [19]). Using this basic mechanism we were able to prepare azlactone derivatives of N-acetyland N-myristoylglycine by reaction with p-nitrobenzaldehyde.…”

Section: Preparation Of Azlactone Derivatives Of Acylglycinementioning

confidence: 99%

Identification of N-myristoylated proteins by reverse-phase high performance liquid chromatography of an azlactone derivative of N-myristoylglycine

Goddard

Felsted

1988

Biochemical Journal

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A method is presented for the identification of N-myristoylated proteins. N-Myristoyl transferases have an absolute requirement for a free N-terminal glycine. N-Myristoylglycine is released upon mild acid hydrolysis of myristoylated peptides and proteins and its derivitization to a p-nitrobenzylazlactone with subsequent analysis by reverse phase h.p.l.c. enabled its detection to pmol levels. This facilitated the identification of N-terminal myristate in nmol quantities of purified proteins. Using this method we demonstrate that the alpha-subunit of the GTP-binding protein G0 is N-terminally myristoylated.

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“…1. [19]). Using this basic mechanism we were able to prepare azlactone derivatives of N-acetyland N-myristoylglycine by reaction with p-nitrobenzaldehyde.…”

Section: Preparation Of Azlactone Derivatives Of Acylglycinementioning

confidence: 99%

Identification of N-myristoylated proteins by reverse-phase high performance liquid chromatography of an azlactone derivative of N-myristoylglycine

Goddard

Felsted

1988

Biochemical Journal

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“…It has long been known (e.g. Cornforth, 1949 ;Baltazzi, 1955) that strongly activated derivatives such as acid chlorides or anhydrides of a-acylamino acids (e.g. a-benzamidocinnamic acid) are w CH30C0 quite unstable and spontaneously undergo rearrangements into the corresponding oxazolones.…”

Section: Principle Of the Methodsmentioning

confidence: 99%

Spectrophotometric determination of microgram quantities of acetylsalicylic anhydride in acetylsalicylic acid

Bundgaard

1973

Journal of Pharmacy and Pharmacology

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A rapid and convenient method for the determination of an immunogenic impurity in acetylsalicylic acid, acetylsalicylic anhydride, is described. The method is based on the spectrophotometric measurement at 362 nm of 4‐benzylidene‐2‐phenyloxazolin‐5‐one, formed in quantitative yield by allowing acetylsalicylic anhydride, pre‐extracted from the acetylsalicylic acid by a benzene‐aqueous phosphate buffer system, to react with a mixture of pyridine and sodium α‐benzamido‐cinnamate in ethanol for 30 min at 20°. The method is reproducible and permits determination of 0ṁ0005% of acetylsalicylic anhydride in acetylsalicylic acid. Applying the method to nine different commercial acetylsalicylic acid preparations, acetylsalicylic anhydride was found to be present in amounts ranging from 0ṁ0012 to 0ṁ024%.

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“…In 1883 a very important variation is done by plӧchl, which involve the heating of benzaldehyde and hippuric acid in presence of acetic anhydride [4]. Erlenmeyer determine the Azalactone structure of the product (Equation 4) and extended the scope of Perkin reaction to other aldehydes (Erlenmeyer Azalactone synthesis) [5][6][7][8][9][10]. Azalactone or oxazolone acts as important intermediate for the synthesis of αamino acid and α-keto acid (Scheme 1).…”

Section: Equation 1 Equation 2 Equationmentioning

confidence: 99%

A Concise Introduction of Perkin Reaction

Rabbani¹

2018

Organic Chem Curr Res

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The chemistry of 5-oxazolones

Abstract: THE condensation of aromatic aldehydes with hippuric acid was discovered in 1883 by Plochl.1 This reaction (1) proved to be one of the most satisfactory of general synthetic methods, and its products, the " azlactones ", are quite valuable intermediates.

Cited by 53 publications

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Identification of N-myristoylated proteins by reverse-phase high performance liquid chromatography of an azlactone derivative of N-myristoylglycine

Identification of N-myristoylated proteins by reverse-phase high performance liquid chromatography of an azlactone derivative of N-myristoylglycine

Spectrophotometric determination of microgram quantities of acetylsalicylic anhydride in acetylsalicylic acid

A Concise Introduction of Perkin Reaction

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