The article contains sections titled: 1. Introduction and History 2. Properties 2.1. Physical Properties and Structure 2.2. Chemical Properties 2.3. Important Amino Acids 2.3.1. Proteinogenic Amino Acids 2.3.2. Other Important Amino Acids 3. Industrial Production of Amino Acids 3.1. General Methods 3.2. Production of Specific Amino Acids 3.2.1. l ‐Alanine 3.2.2. l ‐Arginine 3.2.3. l ‐Aspartic Acid and Asparagine 3.2.4. l ‐Cystine and l ‐Cysteine 3.2.5. l ‐Glutamic Acid 3.2.6. l ‐Glutamine 3.2.7. l ‐Histidine 3.2.8. l ‐Hydroxyproline 3.2.9. l ‐Isoleucine 3.2.10. l ‐Leucine 3.2.11. l ‐Lysine 3.2.12. d , l ‐Methionine and l ‐Methionine 3.2.13. l ‐Phenylalanine 3.2.14. l ‐Proline 3.2.15. l ‐Serine 3.2.16. l ‐Threonine 3.2.17. l ‐Tryptophan 3.2.18. l ‐Tyrosine 3.2.19. l ‐Valine 4. Biochemical and Physiological Significance 5. Uses 5.1. Human Nutrition 5.1.1. Supplementation 5.1.2. Flavorings, Taste Enhancers, and Sweeteners 5.1.3. Other Uses in Foodstuff Technology 5.2. Animal Nutrition 5.3. Pharmaceuticals 5.3.1. Nutritive Agents 5.3.2. Therapeutic Agents 5.4. Cosmetics 5.5. Agrochemicals 5.5.1. Herbicides 5.5.2. Fungicides 5.5.3. Insecticides 5.5.4. Plant Growth Regulators 5.6. Industrial Uses 6. Chemical Analysis 7. Economic Significance 8. Toxicology

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Reaction of L-5-oxoproline esters l-2 with phosgene at 0 °C gives L-5,5-dichloro-l-(chlorocarbonyl)proline esters l-6, which readily lose hydrogen chloride to form L-5-chloro-l-(chlorocarbonyl)-4,5-dehydroproline esters l-7.Catalytic hydrogenation (Pd/C, 180 bar) of l-7 yields L-l-(chlorocarbonyl)proline esters l-15 and thence, upon hydrolysis, L-proline (L-17). A "one-pot reaction" for the whole sequence is described, starting from easily accessible L-5-oxoproline esters and yielding L-proline in 78% overall yield and 99.7% optical purity.

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Racemic S‐(carboxymethyl)cysteine [(R, S)‐2] obtained from racemic cysteine is resolved via its ammonium salt (R, S)‐3 by preferential crystallization procedure. Furthermore, (R, S)‐2 forms with optically active amines separable, diastereomeric salts. Thus, (1R,2S)‐2‐amino‐1‐phenyl‐1‐propanol (4) affords optically pure (R)‐S‐(carboxymethyl)cysteine [(R)‐2] in 93% yield. The resolution of (R, S)‐2 is also possible with (R)‐1‐phenylethylamine (5).