Synthesis amino acid conjugates

Jackson HL, Cardounel AJ, Zweier JL, and Lockwood SF. 2004. Synthesis, characterization, and direct aqueous superoxide anion scavenging of a highly water-dispersible astaxanthin-amino acid conjugate. Bioorganic Medicinal Chemistry Letters 14(15) 3985-3991. 

The vitro synthesis of amino acid conjugates has not been demonstrated with enzyme systems Isolated from plants in spite of the great Importance of these enzymes to our understanding of the mode of action and metabolism of lAA, NAA, and 2,4-D (56). However, it appears that these enzymes can be Induced by exogenous 2,4-D,... 

Table X. Synthesis of amino acid conjugates of exogenous carboxylic acids.

In the late 1960s and into the mid-1970s new synthetic reports appeared in the literature. Most of these focused on the total synthesis of naturally occurring pyranosyl sugar amino acid conjugates. Then, in 1976, Fuchs and Lehmann published the first synthesis of sugar amino acids amidically linked in a fashion similar to a-amino acids. Surprisingly, this disclosure received little attention for nearly 20 years. 

In 1995 Nicolaou and coworkers initiated a renaissance in the construction of sugar amino acid conjugates with their synthesis of carbonucleotoids [49]. Although they did not prepare amide-linked carbohydrates, they did introduce the term carbopep-toid to designate such materials. Shortly thereafter, a number of papers directed toward the synthesis of carbopeptoids appeared. One of the earliest was reported by Wessel et al., who used nor-muramic acid derivatives and condensed them in solution by means of 2-chloro-4,6-dimethoxy-l,3,5-triazine (CDMT) in DMF to construct a tetramer (Fig. 27). 

Recently, the synthesis of l,l -bis(rert-butoxycarbonylamino)ferrocene 52 was reported, a convenient synthon of 1,1 -diaminoferrocene 30, which circumvents the problems encountered with the explosive diazide. The bis-Boc derivative is compatible with the peptide synthesis protocol, as is demonstrated by the preparation of its first amino acid conjugates. 1,1 -Bis(carbonylazido)ferrocene was synthesized from l,l -ferrocenedicarboxylic acid 7 by... 

Scheme 24 Synthesis of bisurea-amino acid conjugates 166-168...

Figure 8.6 Enzymatic synthesis of amino acid-based surfactants (I) linear, (II) dimeric or gemini and (III) diacylglycerol amino acid conjugates. The amino acid can be coupled to an alkyl chain via an ester or an amide linkage.

The amino acid 58 was used in the solid-phase synthesis of sequence-specific DNA binding polyamides containing N-methylimidazole and N-methylpyrrole amino acids <96JACS6141> and it was also reported that the imidazole-acridine conjugate 59 could effectively catalyze the cleavage of t-RNA <96TL4417>. 

Haase C, Seitz O (2007) Chemical Synthesis of Glycopeptides. 267 1-36 Hahn F, Schepers U (2007) Solid Phase Chemistry for the Directed Synthesis of Biologically Active Polyamine Analogs, Derivatives, and Conjugates. 278 135-208 Hansen SG, Skrydstrup T (2006) Modification of Amino Acids, Peptides, and Carbohydrates through Radical Chemistry. 264 135-162... 

Fernandes MJG, Gonfalves MST, Costa SPG (2008) Neurotransmitter amino acid - oxo-benzo[/]benzopyran conjugates synthesis and photorelease studies. Tetrahedron 64 11175-11179... 

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