Djenkolic acid

L-Djenkolic acid was identified as a precursor for CS2 formation in Mimosa pudica, undergoing hydrolysis with a S-alkylcysteine lyase. The actual... 

Lenthionine has the characteristic shiitake flavor. It is formed from the precursor, lentinic acid 14 by complex reactions involving a C-S lyase enzyme.30 Cyclic polysulfides occur in other Basidiomycete mushrooms (Genus Micromp-hale and Colly bid), in some red alga, and in seeds of Parkia speciosa. The latter contain lenthionine and 1,2,4-trithiolane (1,2,4-trithiacyclopentane) 17 as well as compounds with 4, 5, or 6 sulfur atoms.31 These seeds are valued in Indonesia for a unique, onion-like odor. Djenkolic acid and dichrostachinic acid S -[(2-carboxy-2-hydroxyethylsulfonyl)-methyl]cysteine are converted by a C-S lyase enzyme to cyclic polysulfides djenkolic acid yields 1,2,4-trithiolane and 1,2,4,6-tetrathiepane the latter is also formed from dichrostachinic acid.32... 

In structural terms, djenkolic has two units of L-cysteine joined through a CH2 group linked to sulfur atoms. It has also been found in seeds of Albizzia lophanta and Parkia speciosa32 and, as noted earlier, is the source of CS2 in Mimosa pudica (Section 11.1.2.2.2). An enzyme in A. lophanta seeds converted djenkolic acid to an unstable material with a leek-like odor, methylene dithiol 39.92 This was presumably an elimination of aminoacrylic acid 28 via intermediates 37 and 38 (Scheme 13). The methylene dithiol decomposed to H2S and possibly, thioformaldehyde, CH2S the latter might be a source for polysulfides. 

Scheme 13 Formation of methylene dithiol from djenkolic acid...

Djenkolic acid - cysteine-derived amino 121 acid with nephrotoxicity... 

I. Inorganic sulfur compounds containing another (usually more electropositive) element. When the other element is an alkali or alkaline earth, the sulfide is ionic in character. Metal sulfides often have unusual stoichiometries. Examples of sulfides include H2S, Na2S, FeS, and HgS. 2. Organic sulfides are also referred to as thioethers and have the general structure R—S—R. Biochemical examples of sulfides include methionine, cystathionine, and djenkolic acid. If the two R groups are identical, the substance can be referred to as a symmetrical sulfide (biological examples of which are lanthionine and homo-lanthionine). 

Djenkolic acid [498-59-9] M 254.1, m 300-350 (dec). Crystd from a large volume of water. 

Figure 7.11 (Continued) (c) Occurrence of non-protein amino acids (NPAAs). Key to branches leading to families that accumulate pipecolic acid and derivatives (Lens) pipecolic acid and djenkolic acids (Acacia) canavanine others NPAAs. See also legend (a).

S-Alkylcysteine C-S Lyase (EC 4.4.1.6). The endosperm of seeds of the shrub Albizzia lophanta contains djenkolic acid (HOOCCH(NH2)-CH2SCH2SCH2CH(NH2)C00H) and an enzyme which cleaves it to pyruvate, ammonia, and highly odoriferous substances (CH2(SH)2 ) (48, 49). The enzyme has been purified 200-fold by acid and heat treatment, (NH4)2S04 precipitation, and adsorption on alumina (50). It has a broad specificity and cleaves S-derivatives of L-cysteine, its sulfoxide, and sulfone. L-Cysteine itself is cleaved to pyruvate, HjS, and ammonia. 

Piluk J., Hartel P. G., and Haines B. L. (1998) Production of carbon disulfide (CS2) from L-djenkolic acid in the roots of Mimosa pudica L. Plant Soil 200, 27-32. 

Djenkolic acid (S,S -methyIene-bis-L-cysteine) [498-59-9] M 254.3, m 300-350 (dec), [a]g -65 (c 2, HCl) [See pK of S-methyl-L-cysteine]. Crystallise djenkolic acid from a large volume of water (solubility is 0.5g%). [du Vigneaud Patterson J Biol Chem 114 533 1936, Greenstein Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2682, 2687 1961, Beilstein 4 III 1591.] The NJ9 -dibenzoyl derivative crystallises with IH2O from aqueous EtOH with m 87.5-89° [Beilstein 9 III 1171.]... 

This paper (S4) compares the two silylating reagents bis (trimethyl-silyl) acetamide (BSA), first described by Klebe et ad. (K6), and bis-(trimethylsilyl) trifluoroacetamide (BSTFA), for the preparation of volatile trimethylsilyl (TMS) derivatives of 12 sulfur-containing amino acids. BSTFA was recommended as the reagent of choice for taurine, cysteic acid, homocystine, djenkolic acid, ethionine, methionine sulfone, L-2-thiolhistidine, cysteine, and cystine. For S-methyl-L-cysteine, methionine sulfoxide, and methionine, BSA was used as silylating reagent. 

Methionine, methionine sulfoxide, methionine sulfone, S-methyl cysteine Cysteine, cystine, homocysteine, lanthionine, djenkolic acid Lanthionine, djenkolic acid... 

Proteins, polypeptides, cystine, cysteine, glutathione Methionine, methionine sulfoxide, methionine sulfone, S-methyl cysteine Methionine, methionine sulfoxide, methionine sulfone, S-methyl cysteine, homocysteine Methionine, methionine sulfoxide, methionine sulfone, S-methyl cysteine Cysteine, cystine, homocysteine, lanthionine, djenkolic acid Lanthionine, djenkolic acid... 

The chiroptical properties of a number of sulfur-containing amino acids (cysteine or cystine derivatives, such as lanthionine, cystathionine, allo-cystathionine, djenkolic acid, felinine, and S-alkylcysteines) have been described (Coleman and Blout, 1968 Casey and Martin, 1972 Jung et aL, 1973 Takagi et al, 1973 Ottnad et ai, 1975) and correlated with the chiroptical characteristics of the parent compounds. 

A very similar enzyme to that of A. lophanta was purified to homogeneity from extracts of acetone powders of hypocotyls of 5-8 day seedlings of Acacia farnesiana (Mazelis and Creveling, 1975). Since djenkolic acid is a natural constituent in this plant, the activity of this enzyme on this substrate... 

Djenkolic acid residues are formed from cysteine residues when reduced wool is treated with formaldehyde. 

Djenkolic acid (S,S -methylene-bis-L-cysteine) [498-59-9] M 254.3, m 300-350°(dec), [a] -65" (c 2, HCl) [See pK of S-methyl-L-cysteine]. Crystallise djenkolic acid from a large volume of water (solubihty is... 

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