Hydroxylysine total

Hydroxylysine (328) was synthesized by chemoselective reaction of (Z)-4-acet-oxy-2-butenyl methyl carbonate (325) with two different nucleophiles first with At,(9-Boc-protected hydroxylamine (326) under neutral conditions and then with methyl (diphenylmethyleneamino)acetate (327) in the presence of BSA[202]. The primary allylic amine 331 is prepared by the highly selective monoallylation of 4,4 -dimethoxybenzhydrylamine (329). Deprotection of the allylated secondary amine 330 with 80% formic acid affords the primary ally-lamine 331. The reaction was applied to the total synthesis of gabaculine 332(203]. 

NMR. The 300 MHz iR-spectrum of V-2 in D2O is shown in figure 5a. The three multiplets between 1.4 and 2.05 ppm, the two double doublets between 3.4 and 3.7 ppm, and the multiplet between 3.6 and 3.8 ppm comply well with a hydroxylysine substituent at a ring nitrogen (fig. 5b, table 2). No definite conclusion as to the total number of protons can be drawn from the spectrum, since impurities seem to be present, for example singlets at 2.2, 2.05 and 1.95 ppm. The compound V-2 was purified further by ion exchange- and adsorption chromatography and a 500 MHz ID iH- (fig. 6b) and a 2D TOCSY-spectrum (in D2O) were run. Also here, the main spin system present is the hydroxylysine residue (fig. 5b). 

Maurer PJ, Miller Ml (1982) Microbial Iron Chelators Total Synthesis of Aerobactin and its Constituent Amino Acid, if -Acetyl-lf -hydroxylysine. J Am Chem Soc 104 3096... 

PJ Maurer, MJ Miller. Microbial iron chelators total synthesis of aerobactin and its constituent amino acid,N6-acetyl-N6-hydroxylysine. J Am Chem Soc 105 240-245, 1983. 

Electrostatic properties A collagen molecule has a total of approximately 240 e-amino and guanidino groups of lysines, hydroxylysines, and arginines and 230 carboxyl groups of aspartic and glutamic acids. 

Vertebrate collagens have hydroxylysine residues to which the carbohydrate residues are attached. Invertebrate collagens usually lack hydroxylysine and use the hydroxy groups of serine and threonine to attach their carbohydrate residues. Thus, in addition to other criteria mentioned above for the identification of invertebrate collagen, the almost total absence of hydroxylysine and the presence of large amounts of serine and threonine can be added. 

Microbial Iron Chelators Total Synthesis of Aerobactin and Its Constituent Amino Acid, N -Acetyl-N -hydroxylysine. J. Amer. Chem. Soc. 104, 3096 (1982). Kanai, F., K. Isshiki, Y. Umezawa, H. Morishima, H. Naganawa, T. Takita, T. Takeuchi, and H. Umezawa Vanoxonin, a New Inhibitor of Thymidylate Synthetase. II. Structure Determination and Total Synthesis. J. Antibiotics 38, 31 (1985). 

Disorder Hydroxylysine (P) imol/l Free hydroxylysine (U) Total hydroxylysine (U) mmol/mol creat mmol/iuol creat... 

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