New Naturally Occurring Amino Acids

The majority of the 500 or so naturally occurring amino acids known today were discovered during the last 30 years, for example during the search for new antibiotics in the culture media of microorganisms, or as components of the antibiotics in fungi, seeds, in numerous plants and fruits, and in the body fluids of animals. Some 240 of these amino acids occur free in nature, some only as intermediates in metabolism. This article provides an overview of the developments that have taken place in this area since 1956 when the last review appeared. Summary accounts are presented, dealing with new unsaturated amino acids, cyclopropane- and cyclobutane-amino acids, heterocyclic amino acids, halogen-containing amino acids sulfur-, selenium- and phosphorus-containing amino acids as well as aliphatic amino acids. In a few cases, e. g. betalamic acid and muscaflavin, the biosynthesis is described in detail.

[1]  Pamela Zurer Archaeological Chemistry: Physical science helps to unravel human history , 1983 .

[2]  Y. Fujita γ-Hydroxyarginine, a New Guanidino Compound from a Sea-cucumber II. Determination of the Configuration , 1960 .

[3]  Takeshi Matsumoto,et al.  The structure of coronatine , 1977 .

[4]  U. Schmidt,et al.  Total synthesis of zizyphine A. Synthesis of peptide alkaloids. 8. Amino acids and peptides. 40 , 1983 .

[5]  C. Carrano,et al.  Coordination chemistry of microbial iron transport compounds. 16. Isolation, characterization, and formation constants of ferric aerobactin , 1979 .

[6]  R. C. Pandey,et al.  Letter: Berninamycin. I. The structure of berninamycinic acid. , 1976, Journal of the American Chemical Society.

[7]  A. Dreiding,et al.  Biosynthesis of betalaines. On the cleavage of the aromatic ring during the enzymatic transformation of dopa into betalamic acid. , 1972, Helvetica chimica acta.

[8]  T. Kitahara,et al.  The Structure and Synthesis of Aeruginoic Acid (2-o-Hydroxyphenylthiazole-4-carboxylic Acid) , 1970 .

[9]  S. Mizuhara,et al.  Structure of a new sulfur-containing amino acid. , 1962, Archives of biochemistry and biophysics.

[10]  F. Kerek,et al.  Bestimmung der absoluten Konfiguration von Aminen , 1975 .

[11]  P. Scheuer,et al.  Synthesis of α-methylene-β-alanine and one of its naturally occurring α-ketomides , 1980 .

[12]  H. Wieland,et al.  Über die Giftstoffe des Knollenblätterpilzes. V. Zur Konstitution des Phalloidins , 1940 .

[13]  H. Musso,et al.  Fliegenpilzfarbstoffe, VIII1) Die Konstitution der Musca‐aurine , 1982 .

[14]  R. Gennis,et al.  EPR evidence on the structure of the copper(II)-bacitracin A complex , 1983 .

[15]  R. C. Pandey,et al.  BERNINAMYCIN. 2. PRODUCTS OF ACIDIC HYDROLYSIS, METHANOLYSIS, AND ACETOLYSIS OF BERNINAMYCIN A , 1977 .

[16]  D. Janzen,et al.  2,4-Methanoproline (2-carboxy-2,4-methanopyrrolidine) and 2,4-methanoglutamic acid (1-amino-1,3-dicarboxycyclobutane) in seeds of Ateleia herbert smithii Pittier (Leguminosae) , 1980 .

[17]  E. Bayer,et al.  Strukturermittlung der Vanadiumverbindung des Fliegenpilzes, Amavadin , 1973 .

[18]  H. Zähner,et al.  Stoffwechselprodukte von Mikroorganismen. 193. Mitteilung. Ferrithiocin , 1980 .

[19]  Y. M. Sheikh,et al.  Anthopleurine: a sea anemone alarm pheromone. , 1975, Science.

[20]  W. Oppolzer,et al.  Enantioselective synthesis and absolute configuration of (-)-.alpha.-kainic acid , 1982 .

[21]  B. Samuelsson Leukotrienes: mediators of immediate hypersensitivity reactions and inflammation. , 1983, Science.

[22]  A Wendel,et al.  The refined structure of the selenoenzyme glutathione peroxidase at 0.2-nm resolution. , 1983, European journal of biochemistry.

[23]  H. Musso,et al.  Hydrolytischer Abbau der Geomycine; Geomycin, III. Mitteil.: Antibiotica aus Actinomyceten. XXX. Mitteil , 1955 .

[24]  M. Buděšínský On the normalizing factor for the tomato mutant chloronerva. XI. mass and NMR spectroscopic investigations of the phytosiderophore nicotianamine and some of its derivatives , 1981 .

[25]  S. Hecht,et al.  Total synthesis of bleomycin , 1982 .

[26]  M. Pirrung Total Synthesis of 2,4-methanaproline , 1980 .

[27]  H. Musso,et al.  Fliegenpilzfarbstoffe, VII. Konstitution und Synthese des Muscaflavins , 1981 .

[28]  B. McCarry,et al.  A facile synthesis of muscimol , 1982 .

[29]  W. Oppolzer,et al.  High Asymmetric Induction in Lewis Acid‐Promoted Intramolecular Ene‐Type Reactions: A diastereo‐ and enantioselective synthesis of (+)‐α‐allokainic acid. Preliminary Communication , 1980 .

[30]  H. Musso SELECTIVE HYDROGENOLYSIS OF C-C BONDS IN SMALL RING COMPOUNDS , 1983 .

[31]  H. Musso,et al.  Hydrogenolyse kleiner Kohlenstoffringe, VII. Die selektive Hydrierung 1,1‐disubstituierter Cyclopropanderivate , 1980 .

[32]  T. Nakajima,et al.  [STUDIES ON THE CONSTITUENTS OF INDIGENOUS FUNGI. II. ISOLATION OF THE FLYCIDAL CONSTITUENT FROM AMANITA STROBILIFORMIS]. , 1964, Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.

[33]  S. E. Thomas,et al.  Fish attractants from marine invertebrates: Arcamine from Arca Zebra and strombine from Strombus Gigas , 1975 .

[34]  V. Jäger,et al.  A Short Synthesis of Muscimol , 1982 .

[35]  D. Pierson,et al.  Dual enzymatic routes to L-tyrosine and L-phenylalanine via pretyrosine in Pseudomonas aeruginosa. , 1977, The Journal of biological chemistry.

[36]  T. Wieland,et al.  Synthese von zwei diastereomeren natürlichen Dihydroxyprolinen: 2,3‐trans‐3,4‐trans‐3,4‐Dihydroxy‐L‐prolin und 2,3‐cis‐3,4‐trans‐3,4‐Dihydroxy‐L‐prolin , 1981 .

[37]  E. Gil-av,et al.  Separation of enantiomers on packed columns containing optically active diamide phases. , 1975, Journal of chromatography.

[38]  H. Hagenmaier,et al.  Konfiguration von 2‐Amino‐4‐hydroxy‐4‐(5‐hydroxy‐2‐pyridyl)‐3‐methylbuttersäure, der N‐terminalen Aminosäure der Nikkomycine , 1980 .

[39]  O. Hensens,et al.  Structure and absolute configuration of thienamycin , 1978 .

[40]  S. Christensen,et al.  STRUCTURAL ANALOGS OF GABA. A NEW CONVENIENT SYNTHESIS OF MUSCIMOL , 1976 .

[41]  K. R. Woods,et al.  Separation of dansyl-amino acids by polyamide layer chromatography. , 1967, Biochimica et biophysica acta.

[42]  R. Arlinghaus,et al.  3-Hydroxyproline, a new amino acid of collagen. , 1962, The Journal of biological chemistry.

[43]  J. P. Dickie,et al.  The Chemistry of Antimycin A. X. Structure of the Antimycins1 , 1961 .

[44]  Albrecht Lieberknecht,et al.  Aminosäuren und peptide - XXXXII. Synthese von Chlamydocin + epi-Chlamydocin , 1983 .

[45]  F. Weygand,et al.  N‐Trifluoracetyl‐aminosäuren, XVIII. Dampfdruckmessungen an N‐TFA‐Aminosäuren, ‐Peptiden und ihren Estern , 1960 .

[46]  Takeshi Matsumoto,et al.  Isolation and structure of clithioneine, a new amino acid betaine from . , 1981 .

[47]  G. Snatzke,et al.  Determination of the Absolute Configurationof Amines , 1975 .

[48]  A. V. Robertson,et al.  Isolation, Configuration, and Synthesis of Natural cis- and trans-3-Hydroxyprolines , 1963 .

[49]  S. Weiner,et al.  Dead Sea Scroll parchments: unfolding of the collagen molecules and racemization of aspartic acid , 1980, Nature.

[50]  F. Maggio,et al.  The magnetic susceptibility of molten nickel (II) complexes , 1958 .

[51]  J. Bagli,et al.  Elucidation of structure and stereochemistry of myriocin. A novel antifungal antibiotic. , 1973, The Journal of organic chemistry.

[52]  H. Musso Über Phenol‐Oxydationen , 1963 .

[53]  T. Nakajima,et al.  [STUDIES ON THE CONSTITUENTS OF INDIGENOUS FUNGI. I. ISOLATION OF THE FLYCIDAL CONSTITUENT FROM TRICHOLOMA MUSCARIUM]. , 1964, Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.

[54]  M. Suzuki,et al.  A new synthesis of racemic coronamic acid and other cyclopropyl amino acids , 1984 .

[55]  Y. S. Kim,et al.  An N-acetylgalactosaminyltransferase from human blood group A plasma. I. Purification and agarose binding properties. , 1974, The Journal of biological chemistry.

[56]  J. Lyga,et al.  Synthesis of chain-extended and C-6' functionalized precursors of the nucleoside antibiotic sinefungin , 1983 .

[57]  J. Nagy,et al.  Direct synthesis of the antitumor agent erythro-α-amino-3-bromo-4,5-dihydroisoxazole-5-acetic acid , 1980 .

[58]  T. Takemoto,et al.  Avenic acid, a new amino acid possessing an iron chelating activity , 1980 .

[59]  SetoYasuhiko,et al.  Studies of Unusual Amino Acids and Their Peptides. V. The Synthesis and the Absolute Configuration of β(2-Thiazolyl)-β-alanine Present in Bottromycin , 1974 .

[60]  D. van der Helm,et al.  Structure of ferric pseudobactin, a siderophore from a plant growth promoting Pseudomonas. , 1981, Biochemistry.

[61]  H. Brückner,et al.  (−)-isovaline: confirmation of its D-(R)-configuration by X-ray analysis of its N-chloroacetyl derivative , 1982 .

[62]  B. Samuelsson From studies of biochemical mechanism to novel biological mediators: prostaglandin endoperoxides, thromboxanes, and leukotrienes. Nobel Lecture, 8 December 1982. , 1983, Bioscience reports.

[63]  W. König,et al.  Synthese der N‐terminalen Aminosäure der Nikkomycine I, J, X und Z , 1982 .

[64]  F. Weygand,et al.  N‐Trifluoracetyl‐aminosäuren, XV. Trennung von Aminosäuren durch fraktionierte Destillation ihrer N‐Trifluoracetyl‐methylester , 1959 .

[65]  R. Parry,et al.  Determination of the absolute configuration of (−)-S-(2-carboxypropyl)-L-cysteine , 1983 .

[66]  M. Piattelli,et al.  Biosynthesis of indicaxanthin in opuntia ficus-indica fruits☆ , 1972 .

[67]  Y. Guillou,et al.  A new phosphagen, N'-phosphorylguanidinoethylphospho-O-( -N,N-dimethyl)serine (phosphothalassemine). , 1972, Biochemistry.

[68]  L. Jaenicke,et al.  Darstellung von 3‐(3‐Indolyl)milchsäuren. _Eine neue Synthese von rac‐Blepharismon, dem niedermolekularen Konjugationsgamon von Blepharisma japonicum , 1983 .

[69]  U. Groth,et al.  Asymmetrische Synthesen über heterocyclische Zwischenstufen, V Asymmetrische Synthese von α‐Methylaminosäuren durch Alkylieren des lithiierten Lactimethers von cyclo‐(L‐Ala‐L‐Ala) , 1981 .

[70]  E. Gil-av,et al.  Interaction between asymmetric solutes and solvents. Peptide derivatives as stationary phases in gas liquid partition chromatography. , 1970, Tetrahedron.

[71]  Gray Wr,et al.  THE STRUCTURE OF A CHYMOTRYPTIC PEPTIDE FROM PSEUDOMONAS CYTOCHROME C-551. , 1963 .

[72]  N. Amrhein,et al.  Identification of a major metabolite of the ethylene precursor 1-aminocyclopropane-1-carboxylic acid in higher plants , 1981, Naturwissenschaften.

[73]  L. Hurley Elucidation and formulation of novel biosynthetic pathways leading to the pyrrolo[1,4]benzodiazepine antibiotics anthramycin, tomaymycin, and sibiromycin , 1980 .

[74]  H. Akiyama,et al.  Component Amino Acids of the Antibiotic Longicatenamycin. Isolation of 5-Chloro- D -tryptophan , 1975 .

[75]  H. Musso Phenol Oxidation Reactions , 1963 .

[76]  B. Samuelsson The Leukotrienes, Highly Biologically Active Substance Involved in Allergy and Inflammation , 1982 .

[77]  M. d’Ischia,et al.  Isolation and structure of a new sulphur-containing aminoacid from sea urchin eggs , 1982 .

[78]  H. Musso,et al.  Neue natürliche Aminosäuren , 1956 .

[79]  C. Ireland,et al.  Absolute configuration of thiazole amino acids in peptides , 1983 .

[80]  M. Schlosser,et al.  Transmetalation and Double Metal Exchange: A Convenient Route to Organolithium Compounds of the Benzyl and Allyl Type , 1973 .

[81]  Takeshi Matsumoto,et al.  Isolation and structure of aromelic acid A and B. New kainoids of , 1983 .

[82]  Marvin J Miller,et al.  Total synthesis of a mycobactin: mycobactin S2 , 1983 .

[83]  H. Musso The pigments of fly agaric, Amanita muscaria , 1979 .