AMINO ACIDS PEPTIDES AND PROTEINS VOLUME 2 (HB 1970)

YOUNG G.

ISBN 10: 0851860141 / ISBN 13: 9780851860145

Verlag: SP RSC PUBLISHING, 1970

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Amino-Acids, Peptides, and Proteins Volume 2

A Review of the Literature Published During 1969

By G. T. Young

The Royal Society of Chemistry

Copyright © 1970 The Chemistry Society
All rights reserved.

ISBN: 978-0-85186-014-5

Contents

Chapter 1 Amino-acids By B. W. Bycroft, 
Chapter 2 Structural Investigation of Peptides and Proteins, 
Chapter 3 Peptide Synthesis By J. H. Jones, 
Chapter 4 Peptides with Structural Features Not Typical of Proteins By J. S. Davies, 
Chapter 5 Extracts from the Tentative Rules of the 1.U.P.A.C.-I.U.B. Commission on Biochemical Nomenclature, 

CHAPTER 1

Amino-acids

By B. W. BYCROFT

The presentation of this chapter conforms, in general, to the pattern established in last year's Report. New amino-acids with novel structures continue to be isolated from natural sources and the chemistry of amino-acids still attracts considerable attention from all branches of the subject. The emphasis remains on a-amino-acids and it is only for these that a comprehensive coverage has been attempted. Biochemical aspects have been covered only where they relate directly to the chemistry.

1 Naturally Occurring Amino-acids

A. Introduction. — The literature on non-protein naturally occurring amino-acids has been reviewed up to the end of 1968 in a valuable article which also discusses their probable origin and function. Speculation concerning the origin of D-amino-acids continues: the observation that for amino-acids containing more than one centre of chirality inversion of configuration occurs only at the α-centre has led to the rule of α-epimerisation. Amino-acids have been isolated during the year which conform to the rule, together with one apparent exception (see below). Two possible explanations to account for the origin of D-amino-acids, both of which accommodate most of the known information relating to D-amino-acids and are in accord with the above described rule, have been proposed.

B. New Free Occurring Amino-acids. — The continuing usefulness of physical methods in structural elucidation is apparent, and several new amino-acids have been characterised during the year. Those whose structure has been confirmed by synthesis are included in the list of newly synthesised amino-acids in section 2. Especially noteworthy is the characterisation by spectroscopic methods of the novel amino-acid (1), which is produced by Claviceps species inhibited with ethionine and is probably an intermediate in the biosynthesis of lysergic acid. Several other amino-acids have also been isolated from fungi or micro-organisms. The mushrooms Morchella esculenta and related species produce cis-3-amino-L-proline. β-Methylene-L-norvaline has been obtained from Lactarius helvus,s and the closely related allenic amino-acid (2) occurs in Amanita solitaria? A new sulphur-containing amino-acid (3) from Xeromus subtomentosus has been reported, but this is probably a modified dipeptide derived from glutamic acid and cysteine. The antimetabolic antibiotic (4), produced by an unidentified Streptomyces species, has been shown to be active against Gram-positive organisms.

A number of new plant amino-acids have been described. The phyto-chemical similarities between Aesculus and Blighia species have been extended: exo-3,4-methanoproline and cis-α-(carboxycyclopropyl)glycine (5) occur in Aesculus parviflora, while the trans-isomei of (5) is found in Blighia sapida. The structures of three new acetylenic amino-acids (6), (7), and (8) from the seeds of Euphoria longan have been determined and the structure of the pyrimidine amino-acid isolated from pea seedlings has been revised to (9). Selenomethylselenocysteine has been shown to be the principal selenium-containing amino-acid in Astragalus bisulcatus.

C. New Amino-acids from Peptide Hydrolysates. — Hydrolysis of the antibiotic monamycin affords the novel piperidazine amino-acid (10), the structure and absolute configuration of which have been confirmed by a direct correlation with L-ornithine, as well as the structurally related D-amino-acids (11) and (12) (opposite absolute configuration). In addition, D-isoleucine, an exception to the rule of α-epimerisation, has also been isolated from the acid hydrolysate. In contrast, the acid hydrolysates of the antibiotics aspartocin and enduracidin yield L-threo- and D -erythro]-αβ-diaminobutyric acid and enduracididine (13) and ollo-enduracididine (14) respectively; both the D-amino-acids are in accord with the rule. The structure, but not the stereochemistry, of the basic amino-acid stendomycidine (15) has been determined, and the close similarity between it and the previously isolated guanidine amino-acids capreo-mycidine and viomycidine is noteworthy. Further details on the chemistry of viomycidine have been published. Hydrolysis of diatom cell walls affords cis-4-3,4,trans-3,4-dihydroxy-L-proline, the structure of which has been confirmed by an X-ray crystallographic analysis (see section 3). N-(2-Hydroxyethyl) alanine was isolated from the alkali hydrolysate of a phospholipid obtained from rumen protozoa.

D. Occurrence of Known Amino-acids. — β-Cyanoalanine, the neurotoxin, is the product of cyanide fixation and an intermediate in asparagine biosynthesis in a number of Lathyrus and Vicia species. Canaline (L-γ-aminoxy-α-aminobutyric acid) has been obtained from the unripe seeds of Astragalus suricus and trans-3- hydroxy-L-proline from the seeds of Delonix regia. Nα-Acetyl-L-arginine has been reported to be present in cattle brain.

2 Chemical Synthesis and Resolution of Amino-acids

A. Introduction. — The majority of new syntheses, with notable exceptions, were performed by variations of well established routes or involved elaboration of available amino-acids. Therefore, only those syntheses which have points of particular interest will be discussed and the remainder merely mentioned or incorporated into the list of newly synthesised amino-acids.

B. Protein Amino-acids. — New syntheses have been reported for DL-lysine, DL-tryptophan, DL-cystine, d- and L-cysteine, and D-phenylalanine, and the advances in asymmetric synthesis of α-amino-acids reviewed. Both forms of alanine have been obtained from oxaloacetic acid by an asymmetric transamination, and an elegant asymmetric synthesis (Scheme 1) of optically pure L-aspartic acid has been reported. The detailed studies, first reported last year, on the resolution of glutamic acid and alanine by fractional crystallisation have been extended.

C. Other Naturally Occurring Amino-acids. — Interest in L-dopa (3,4-dihydroxyphenylalanine) continues: syntheses from L-tyrosine using crystalline β-tyrosinase and from N-blocked L-tyrosine derivatives employing micro-organisms have been published. DL-Indospicine, the heptatotoxic amino-acid, first reported last year, and all the four isomers of tricholomic acid (16) have been synthesised. Synthetic DL-α-amino-δ -(guanylureido)-n-valeric acid is identical with gigartinine in all respects except optical activity, and the structures of β-methylene-norvaline, the sulphur-containing amino-acid (3), and N-2,3-dihydroxybenzoyl-serine have all been confirmed by synthesis. Reduction of (17) followed by...

Bibliografische Details

Titel: AMINO ACIDS PEPTIDES AND PROTEINS VOLUME 2 (...
Verlag: SP RSC PUBLISHING
Erscheinungsdatum: 1970
Zustand: New
Auflage: Internationale Ausgabe