Sarcosinates

Chloroacetic acid can be esterified and aminated to provide useful chemical intermediates. Amphoteric agents suitable as shampoos have been synthesized by reaction of sodium chloroacetate with fatty amines (4,5). Reactions with amines (6) such as ammonia, methylamine, and trimethylamine yield glycine [66-40-6J, sarcosine [107-97-17, and carhoxymethyltrimethylammonium chloride, respectively. Reaction with aniline forms /V-phenylglycine [103-01 -5] a starting point for the synthesis of indigo (7). 

Surfa.cta.nts, Ai-Acylglutamates, sodium A/-lauroyl sarcosinate [137-16-6] and A/-acyl-alanine Na salt are used in the cosmetic field as nontoxic surfactants (237). Some of them (eg, A/-acylglutamic acid dibutylamide) are used as oil geUating agents to recover efduent oil in seas and rivers (238). 

Fig. 2. Synthesis of uma2enil (18). The isonitrosoacetanihde is synthesized from 4-f1iioroani1ine. Cyclization using sulfuric acid is followed by oxidization using peracetic acid to the isatoic anhydride. Reaction of sarcosine in DMF and acetic acid leads to the benzodiazepine-2,5-dione. Deprotonation, phosphorylation, and subsequent reaction with diethyl malonate leads to the diester. After selective hydrolysis and decarboxylation the resulting monoester is nitrosated and catalyticaHy hydrogenated to the aminoester. Introduction of the final carbon atom is accompHshed by reaction of triethyl orthoformate to...

Almost all actinomycins have the same chromophore, a planar phenoxa2inone dicarboxyUc acid called actinocin. In dactinomycin, the stmcture of which is shown in Figure 12, the two pendent pentapeptide lactones are identical, but in other actinomycins these lactones may be different. In other actinomycins the first amino acid, amide linked with actinocin, is usually L-threonine, as in dactinomycin the second position is sometimes D-aHo-isoleucine instead of D-valine the third position may be sarcosine or oxoproline the fourth position is sarcosine and the fifth position is sometimes /V-methyl isoleucine instead of /V-methylvaline. The lactone ring is always present. 

Fig. 12. Stmcture of dactinomycin (actinomycin D) where MeVal = N-methylvaline and Sar = sarcosine.

Fig. 14. Structure of cyclosporin A where MeBmt = 4-(2-butenyl)-4, A-dimethylthreonine Sar = sarcosine MeLeu = A-methylleucine ...

The surfactant most commonly used is the anionic detergent sodium lauryl sulfate. Other surfactants that have been used include sodium dodecylbenzene sulfonate [25155-30-0] sodium A/-lauroyl sarcosinate or Gardol [137-16-6] and sodium cocomonoglyceride sulfonate [3694-90-4]. Cationic and nonionic surfactants are not used for several reasons, including incompatibiUty with the abrasive system and lack of high foaming capabiUty. 

Sarcosine anhydride [5076-82-4] M 142.2, m 146-147 , pK s ( )-from water, EtOH or ethyl acetate. Dried in vacuum at room temperature. 

Dihydro-2//-pyran-5-carbaldehyde (7) was treated with sarcosine ethylester (2) in the presence of sodium ethoxide. What is the structure of the crystalline product Cii/7/rfN03 given its NMR spectra 27 ... 

Amino-4,6-dimethyl-3-oxo-3//-phenoxazine-l,9-dicarboxylic acid also named actinocin is the chromophor of the red antineoplastic chromopeptide aetinomyein D (formula A). Two cyclopenta-peptide lactone rings (amino acids L-threonine, D-valine, L-proline, sarcosine, and 7V-methyl-L-valine) are attached to the carboxy carbons of actinocin by two amide bonds involving the amino groups of threonine. 

Ornithine, proline, hydroxyproline, pipecolic acid and sarcosine yield red zones, glycine greenish-brown and the other amino acids weakly brown ones [3]. The colors of the zones are different if an alcoholic solution of potassium carbonate is used for basification instead of dipping solution II. 

Properties,—Small rhombic prisms with difficulty soluble m cold water, readily soluble in hot water. On warminy with alkalis, it decomposes iuto urea and sarcosine,... 

Glycocoll.—By the action of primary and secondary amines, corresponding" aniino-acids aie foinied. Chloiacetic acid and methylamine yield sarcosine,... 

Intramolecular cycloadditions of 4/f-pyrido[l,2-n]pyrimidin-4-ones 235 (R = H, Me Ph) and MeNHOH HCl gave tetracyclic isoxazolo derivatives 237. In the case of 235 (R = Me) a minor epimer 238 was also isolated (00JCR(S)414). Similar reaction of 235 (R = H, Me, Ph) and sarcosine ethyl ester HCl afforded an isomeric mixture of epimeric tetracyclic pyrrolo derivatives 239 and 240. In the reaction of 235 (R = H) and PhCHjNHCHjCOOEt only one product 241 was obtained. 

The complex thioamide lolrestat (8) is an inhibitor of aldose reductase. This enzyme catalyzes the reduction of glucose to sorbitol. The enzyme is not very active, but in diabetic individuals where blood glucose levels can. spike to quite high levels in tissues where insulin is not required for glucose uptake (nerve, kidney, retina and lens) sorbitol is formed by the action of aldose reductase and contributes to diabetic complications very prominent among which are eye problems (diabetic retinopathy). Tolrestat is intended for oral administration to prevent this. One of its syntheses proceeds by conversion of 6-methoxy-5-(trifluoroniethyl)naphthalene-l-carboxyl-ic acid (6) to its acid chloride followed by carboxamide formation (7) with methyl N-methyl sarcosinate. Reaction of amide 7 with phosphorous pentasulfide produces the methyl ester thioamide which, on treatment with KOH, hydrolyzes to tolrestat (8) 2[. 

Muskel-. muscular, myo-, -eiweiss, n, myosin, -empfindung, /, muscular sensation, -farb-stoff, m. muscle pigment, -faser,/, muscular fiber, -fleisch, n, muscular substance, -ge-webe, n. muscular tissue, -gift, n, muscle poison, -lehre, /, myology, -masse, /. muscular substance, -saft, m. muscle juice,. -stoff, m. sarcosine. -zucker, m. inositol. Muskowit, Muskovit, m. (Min.) muscovite, muss, pr. 1 tS 3 sing, (of miissen) must. 

Glycine transporter GlyTl (SLC6A9) CNS-glia -20 Clearance of interstitial neurotransmitter Sarcosine... 

The sodium carboxylates resulting from hydrolyzable tannins are similar to the gluconates and sarcosinates commonly employed as... 

Cobalt, tetraamminepyrophosphato-structures, 1, 202, 203 Cobalt, tetraammine(sarcosine)-chirality, 1,198 Cobalt, triammine-structure, 1, 8—10 Cobalt, tricarbonato-reactions, 1,22 Cobalt, tricarbonylnitroso-exchange reactions, 1, 290 Cobalt, trichloro-equilibrium constant, 1, 517 Cobalt, trichlorobis(triethylphosphine)-structure, 1, 45... 

Sodium lauryl sarcosinate is very similar to the lauryl sulfate class of detergents and surfactants. The sulfate group is replaced with the amino acid sarcosinic acid, and the ammonium group is replaced with a sodium atom. The result is a detergent that is milder on the skin and oral membranes, and can be used in toothpastes without causing irritation of the gums. 

Lauryl sulfates can irritate oral membranes, and so a similar detergent, lauryl sarcosinate, often replaces some or all of the lauryl sulfate. Allantoin is sometimes added to relieve irritation caused by detergents, alkalies, and acids. 

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