Novel Formation of α-Amino Acids and Their Derivatives from Oxo Acids and Ammonia in an Aqueous Medium
In the course of a study of chemical evolution in the primeval sea, a novel reaction of carbonyl compounds with ammonia was found. Glyoxylic acid reacted with ammonia to afford N-oxalylglycine, which gave glycine in a 3–20 % yield after 6 n HC1 hydrolysis. Similarly, glyoxylic acid was treated with...
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| Veröffentlicht in: | Journal of biochemistry (Tokyo) 1982-01, Vol.91 (6), p.2087-2090 |
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| container_end_page | 2090 |
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| container_issue | 6 |
| container_start_page | 2087 |
| container_title | Journal of biochemistry (Tokyo) |
| container_volume | 91 |
| creator | YANAGAWA, Hiroshi MAKINO, Yumiko SATO, Kazuki NISHIZAWA, Masato EGAMI, Fujio |
| description | In the course of a study of chemical evolution in the primeval sea, a novel reaction of carbonyl compounds with ammonia was found. Glyoxylic acid reacted with ammonia to afford N-oxalylglycine, which gave glycine in a 3–20 % yield after 6 n HC1 hydrolysis. Similarly, glyoxylic acid was treated with methylamine to give N-oxalylsarcosine, which afforded sarcosine in a 9–12% yield upon hydrolysis. Pyruvic acid reacted with ammonia to give N-acetylalanine, which gave alanine in a 1–4% yield upon hydrolysis. These reactions provide a novel and facile route to a-amino acids and their derivatives. A mechanism for the reactions is proposed. |
| doi_str_mv | 10.1093/oxfordjournals.jbchem.a133902 |
| format | Article |
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Glyoxylic acid reacted with ammonia to afford N-oxalylglycine, which gave glycine in a 3–20 % yield after 6 n HC1 hydrolysis. Similarly, glyoxylic acid was treated with methylamine to give N-oxalylsarcosine, which afforded sarcosine in a 9–12% yield upon hydrolysis. Pyruvic acid reacted with ammonia to give N-acetylalanine, which gave alanine in a 1–4% yield upon hydrolysis. These reactions provide a novel and facile route to a-amino acids and their derivatives. 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| identifier | ISSN: 0021-924X |
| ispartof | Journal of biochemistry (Tokyo), 1982-01, Vol.91 (6), p.2087-2090 |
| issn | 0021-924X 1756-2651 |
| language | eng |
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| source | J-STAGE Free; MEDLINE; Free Full-Text Journals in Chemistry; Oxford University Press Journals Digital Archive Legacy |
| subjects | Amino Acids - chemical synthesis Ammonia Chemical Phenomena Chemistry Glyoxylates |
| title | Novel Formation of α-Amino Acids and Their Derivatives from Oxo Acids and Ammonia in an Aqueous Medium |
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