Neue natürliche Aminosäuren

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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A Novel Approach for the One-Pot Preparation ofα-Amino Amides by Pd-Catalyzed Double Carbohydroamination

Lin¹,

Alper²

2001

Angew. Chem.

17

0

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Developing new synthetic methods for the preparation of amino acids and their derivatives has attracted much attention due to their applications to the fine chemical, agrochemical, and pharmaceutical business sectors. [1] Although a variety of elegant routes has been discovered for the synthesis of amino acids, amidocarbonylation (Wakamatsu reaction) is the only method involving a transition metal complex catalyzed threecomponent reaction of an aldehyde, an amide, and carbon monoxide. [2] Domino reactions, which include amidocarbony-The data in this report, in conjunction with the N-terminal structure of the rapamycin PKS, allow us to identify 4 as the true starter unit for the rapamycin PKS. The differing stereospecificity of the enoyl reductions during the biosynthesis of 1 for FK 520, and by extrapolation for rapamycin, is consistent with the use of the initiation module ER domain. [17] The differences in stereochemical detail between the biosynthesis of 1, [8] and the biosynthesis of CHC [14,15] suggest that precursors of 4 occur as the free acids. [18] By analogy to nonribosomal peptide synthesis [19] we suggest (Scheme 3) that the S S O O S O OH OH OH HO HO HO CO 2 H HO OH CO-AMP HO OH CO-ACP HO OH CL ACP ACP ER KS AT DH ER KR initiation module module 1 CL domain ACP AMP ATP PPi A B 4 Scheme 3. A) Proposed pathway for CL-catalyzed activation and subsequent attachment of 4 to the rapamycin PKS; B) translocation of ACPbound 4 involves reduction of the D 1 bond by the initiation module ER domain prior to chain elongation on module one of RAPS1, the N-terminus of which is shown with a linear arrangement of the predicted catalytically active domains. AMP adenosine monophosphate; Ppi inorganic phosphate; CL carboxylic acid ligase; ER enoyl reductase; ACP acyl carrier protein; KS b-ketoacyl synthase; AT acyl transferase; DH dehydratase; KR b-ketoacyl reductase.CL domain catalyses formation of an AMP-activated form of 4, which is subsequently transferred to the ACP domain. Reduction by the ER domain is followed by transfer to the KS1 domain of RAPS1 to initiate chain elongation. The observation that 1 can also be directly incorporated points to a broad substrate specificity in the CL domain which may allow for its use for the production of analogues of rapamycin by incorporation of a variety of alicyclic starter acids.

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Neue natürliche Aminosäuren

Cited by 74 publications

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Amino Acids

Amino Acids

Amino Acids

A Novel Approach for the One-Pot Preparation ofα-Amino Amides by Pd-Catalyzed Double Carbohydroamination

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