Amino acids glycoconjugated

Click chemistry has been particularly active in various fields this year. For example, ample applications of click chemistry have been seen in carbohydrate chemistry. Various /weiido-oligosacchardies and amino acid glycoconjugates were synthesized via an intermolecular 1,3-dipolar cycloaddition reaction using easily accessible carbohydrate and amino acid derived azides and alkynes as building blocks <06JOC364>. The iterative copper(I)-catalyzed... 

Dondoni, A. Massi, A. (2006) Design and Synthesis of New Classes of Heterocyclic C-Glycoconjugates and Carbon-Linked Sugar and Heterocyclic Amino Acids by Asymmetric Multicomponent Reactions (AMCRs). Accounts of Chemical Research, 39, 451M63. 

Dondoni A, Massi A (2006) Design and synthesis of new classes of Heterocyclic C-glycoconjugates and carbon-linked sugar and heterocyclic amino acids by asymmetric multicomponent reactions (AMCRs). Acc Chem Res 39 451-463... 

Other components described in the literature which are able to enhance saltiness or umami taste are umami-tasting glutamate glycoconjugates (e.g. 18 or 19) [42], (S)-malic acid 1-0-D-glucopyranoside (morelid 20) [43], theogalline (21) [44], M-lactoyl ethanolamine (22) [45] and JV-gluconyl ethanolamines (23) [46], a-keto acids derived from amino acids (e.g. 24) [47] and some N-succinoyl derivatives of aspartic acid or glutamic acid (e.g. 25 and 26) [48]. 

B. LUning, T. Norberg, and J. Tejbrant, Synthesis of mono- and disaccharide amino-acid derivatives for use in solid phase peptide synthesis, Glycoconjugate J. 6 5 (1989). 

The introduction of the chemical handle needed (azide or alkyne) can be achieved by means of indiscriminate functiona.liza.tion of natural amino acids (via Lys [128-131] or Cys [129]) or by genetic incorporation. The latter strategy permits the preparation of more precisely defined glycoconjugates. One comparison of the two methods was... 

Fig. 15. (A) Schematic presentation of the S-layer glycoprotein of Halobacterium halobium, showing the different glycosylation sites and the membrane binding domain at the C-terminal end. Numbering indicates amino acid positions. (B) Schematic presentation of the three different glycoconjugates (BIBS). From ref. [117].

This chapter covers natural glycoconjugates in which carbohydrates are covalently linked to amino acids which themselves are part of a peptide or protein. Three classes of biologically important compounds fulfill this criterion ... 

Glycoconjugates Antitumor and antimicrobial drugs Deoxysugars Molecular recognition Antibiotic resistance Antiadhesives Sugar amino acids Functional glycoconjugates... 

---