Tryptophan chemical structure

FIGURE 5.10 Chemical structures of AB3 self-immolative dendritic molecules with tryptophan tail units and a trigger that is activated by PGA. 

Figure 5.22 Chemical structures of tryptophan and cysteine as subunits of a protein chain...

This compound cluster exhibits a two-ring, "open-chained, indolic chemical structure, and in contrast to other psychedelics it is all but inactive when taken orally unless accompanied by certain other compounds. Shortacting tryptamines are closely related to neurotransmitters (such as bufotenine), to MDA (a major botanical source of the snuffs belongs to the nutmeg family), to tryptophan (an essential amino acid produced in human digestion of proteins) and to psilocybin and psilocin (which are tryptamines of longer duration). DMT, the simplest member, occurs normally in the blood, brain and (in higher concentrations) in the cerebrospinal fluid. 

Figure 4 Chemical structures of tryptophan and of contaminants EBT and PAA associated with EMS.

The incorporation experiments by Birch and co-workers (33,34), using [2- C]mevalonic acid, L-[l- 4C]alanine, and L-tryptophan, provided valuable information for the structural elucidation. Echinulin possesses two asymmetric centers, l-Alanine is obtained by acid hydrolysis, but another chiral center on the tryptophan moiety is easily racemized. Later, it was determined as the l form by microbioassay of the aspartic acid obtained by ozonolysis (35). Finally, the chemical structure 12 was confirmed by the stereoselective total synthesis of optically active echinulin by Kishi and co-workers (36) (Scheme 5). 

Ditryptophenaline (56), mp 204-205°C, was isolated from the mycelium of Asp. flavus during the investigation for food-borne mycotoxin by Biichi and coworkers (104). The chemical formula, C42H4QNg04, is assigned on the basis of the high-resolution mass spectrum (m/z 692.3095), and the NMR spectrum indicates a dimeric structure. It possesses a diketopiperazine ring derived from tryptophan and phenylalanine and has UV absorptions at 244 and 303 nm. The chemical structure was determined by single-crystal X-ray experiments. Later, Hino and co-... 

Fales and Pisano (1964) have discussed the gas chromatography of amines, alkaloids, and amino acids. Pollock and Kawauchi (1968) have resolved derivatives of serine, hydroxyproline, tyrosine, and cysteine, as well as racemic aspartic acid and tryptophan. VandenHeuvel and Horning (1964) have listed derivatives of steroids that can be separated. VandenHeuvel et al. (1960) first described the separation of bile acid methyl esters and Sjovall (1964) has extended the methods to bile acids. Gas liquid chromatography (GLC) is useful in the analysis of pesticides, herbicides, and pharmaceuticals (Burchfield and Storrs, 1962). Analysis of alkaloids, steroids, and mixtures of anesthetics and expired air are other examples of the application of this very useful technique. Beroza (1970) has discussed the use of gas chromatography for the determination of the chemical structure of organic compounds at the microgram level. 

As described previously, the origins of the three types of curare are the extracts of Chondodendron (Menispermaceae) and/or Strychnos (Loganiaceae) plants. Among them, the toxic components of Strychnos plants are C-curarine and C-toxiferine I, etc.These constituents are alkaloids derived from tryptophan and are described in the next (Section 2.15).The C- is the initial of calabash. On the other hand, the toxic principle of tubocu-rare is d-tubocurarine, an alkaloid derived from phenylalanine. The alkaloid was first isolated as a hydrochloride from tubocurare and is preserved in the Museum of the British Society of Pharmacy [1]. The chemical structure of d-tubocurarine was first proposed as a bisbenzylisoquinoline with two quaternary ammonium moieties. This was revised in 1970 to be the structure with one tertiary and one quaternary amine after X-ray crystallographic analysis [2]. 

The chemical structure of heteroauxin was established to be indole-3-acetic acid (indole-P-acetic acid (lAA)). It is considered that lAA is formed by the enzymatic oxidation of indole-3-acetaldehyde derived from tryptophan via indole-3-pyruvic acid or tryptamine. Between these two routes, the main route is thought to be through indole-3-pyruvic acid. 

From this result, it was confirmed that 3-amino-5-hydroxybenzoic acid was the direct biosynthetic precursor of the w-CyN unit of porfiromycin. Because of its chemical structure, it might be thought that tryptophan could be involved in the biosynthesis of the mitomycins, like those alkaloids possessing an indole nucleus, whereas in fact the mitomycins were biosynthesized from an m-CyN unit and a D-glucosamine moiety. 

Most alkaloids have basic properties coimected with a heterocyclic tertiary nitrogen. Notable exceptions are colchicine, caffeine, and paclitaxel. Most alkaloids are biosynthetically derived from amino acids such as phenylalanine, tyrosine, tryptophan, ornithine, and lysine. Alkaloids represent a wide variety of chemical structures. About 20000 alkaloids are known, most being isolated from plants. But alkaloids have also been found in microorganisms, marine organisms such as algae, dinoflagellates, and puffer fish, and terrestrial animals such as insects, salamanders, and toads. 

Fig. 21.5 The chemical structures of the drug carbamazepine and the receptor amino acids phenylalanine and tryptophan...

Fig. 4.14 NEXAFS C K-edge spectra and chemical structures of the six amino acids gUcyne (Gly), phenilalanine (Phe), histidine (His), tyrosine (Tyr), tryptophane (Trp) and arginine (Arg). (Reprinted from Boese et al. [41], Copyright (2009), with permission from Elsevier)...

FIGURE 3.5 Chemical structure of the essential amino adds, (a) Lysine, (b) Tryptophan, (c) Methionine, (d) Threonine, (e) Phenylalanine, (f) Leudne. (g) Isoleudne. (h) Valine, (i) Histidine. 

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