Modified and Modifying Sugars as a New Tool for the Development of Therapeutic Agents - The Biochemically Engineered N-Acyl Side Chain of Sialic Acid: Biological Implications and Possible Uses in Medicine

2005 ◽  
pp. 863-873
Author(s):  
Rüdiger Horstkorte ◽  
Oliver T. Keppler ◽  
Werner Reutter
Keyword(s):  
Sialic Acid ◽  
Therapeutic Agents ◽  
Side Chain ◽  
Acyl Side Chain

scholarly journals Biochemical engineering of the N-acyl side chain of sialic acid: biological implications

Glycobiology ◽  
2001 ◽  
Vol 11 (2) ◽  
pp. 11R-18R ◽  
Author(s):  
O. T. Keppler ◽  
R. Horstkorte ◽  
M. Pawlita ◽  
C. Schmidt ◽  
W. Reutter
Keyword(s):  
Sialic Acid ◽  
Side Chain ◽  
Biochemical Engineering ◽  
Acyl Side Chain

In vivo modulated N -acyl side chain of N -acetylneuraminic acid modulates the cell contact-dependent inhibition of growth

FEBS Letters ◽  
1996 ◽  
Vol 395 (2-3) ◽  
pp. 170-173 ◽  
Author(s):  
J.Raimund Wieser ◽  
Anja Heisner ◽  
Peer Stehling ◽  
Franz Oesch ◽  
Werner Reutter
Keyword(s):  
Side Chain ◽  
Cell Contact ◽  
Acetylneuraminic Acid ◽  
Inhibition Of Growth ◽  
Acyl Side Chain ◽  
Dependent Inhibition

scholarly journals Degradation of the Acyl Side Chain of the Steroid Compound Cholate in Pseudomonas sp. Strain Chol1 Proceeds via an Aldehyde Intermediate

2012 ◽  
Vol 195 (3) ◽  
pp. 585-595 ◽  
Author(s):  
J. Holert ◽  
Z. Kulic ◽  
O. Yucel ◽  
V. Suvekbala ◽  
M. J.- F. Suter ◽  
...  
Keyword(s):  
Side Chain ◽  
Pseudomonas Sp ◽  
Steroid Compound ◽  
Acyl Side Chain

Rashes with Ampicillin

1980 ◽  
Vol 1 (7) ◽  
pp. 197-201
Author(s):  
Michael J. Kraemer ◽  
Arnold L. Smith
Keyword(s):  
Penicillin G ◽  
Side Chain ◽  
Gram Negative Bacteria ◽  
Acid Moiety ◽  
Structure Activity ◽  
Body Tissues ◽  
The Family ◽  
Acyl Side Chain ◽  
Penicillanic Acid ◽  
Lactam Ring

Ampicillin, first introduced in 1961, has probably become the most widely used penicillin in clinical pediatrics. STRUCTURE ACTIVITY RELATIONSHIPS All penicillins contain the 6-amino penicillanic acid moiety (Fig 1). Its structure includes a thiazolidine ring (A), a β-lactam ring (B), the source of antibacterial activity, and an acyl side chain (R), containing a variety of substitutions creating the family of semisynthetic penicillins. The only difference between ampicillin and penicillin G is the presence of an amino group in the acyl side chain (Fig 1). PHARMACOLOGY AND BACTERIOLOGY Ampicillin is a semisynthetic penicillin, active against Streptococus pneumoniae and certain Gram-negative bacteria, including most Haemophilus influenzae, Escherichia coli, and certain Proteus species. Compared to penicillin G, it has increased stability in acid solutions: a property facilitating oral administration and absorption. It penetrates into most body tissues; effective entry into CSF, however, occurs only with inflamed meninges. The serum half-life with normal renal function varies from four hours in newborns1 to 1.3 hours in adults.2 Ampicillin can cause an allergic, or nonallergic skin rash (Fig 2). ALLERGY Allergy (for the purposes of this discussion) is defined as a specific immunologic interaction, between either antigen and antibody, or antigen with a sensitized lymphocyte, resulting in a clinically deleterious effect. Implicit is a prior contact with the antigen.

Biochemical engineering of the acyl side chain of sialic acids stimulates integrin-dependent adhesion of HL60 cells to fibronectin

2002 ◽  
Vol 80 (10) ◽  
pp. 671-677 ◽  
Author(s):  
Pablo Villavicencio-Lorini ◽  
Stephan Laabs ◽  
Kerstin Danker ◽  
Werner Reutter ◽  
Rüdiger Horstkorte
Keyword(s):  
Sialic Acids ◽  
Side Chain ◽  
Biochemical Engineering ◽  
Hl60 Cells ◽  
Acyl Side Chain

scholarly journals Mouse Siglec-1 Mediatestrans-Infection of Surface-bound Murine Leukemia Virus in a Sialic AcidN-Acyl Side Chain-dependent Manner

2015 ◽  
Vol 290 (45) ◽  
pp. 27345-27359 ◽  
Author(s):  
Elina Erikson ◽  
Paul R. Wratil ◽  
Martin Frank ◽  
Ina Ambiel ◽  
Katharina Pahnke ◽  
...  
Keyword(s):  
Murine Leukemia Virus ◽  
Leukemia Virus ◽  
Side Chain ◽  
Dependent Manner ◽  
Acyl Side Chain ◽  
Murine Leukemia

Synthesis of kairomones and their analogs from 2-acylcyclohexane-1,3-diones with an unsaturated acyl side chain

2008 ◽  
Vol 44 (10) ◽  
pp. 1444-1450 ◽  
Author(s):  
F. A. Lakhvich ◽  
I. I. Petrusevich ◽  
N. G. Ogeiko ◽  
A. N. Sergeeva
Keyword(s):  
Side Chain ◽  
Acyl Side Chain ◽  
Unsaturated Acyl

Glycoengineering the N-acyl side chain of sialic acid of human erythropoietin affects its resistance to sialidase

2012 ◽  
Vol 393 (8) ◽  
pp. 777-783 ◽  
Author(s):  
Anselm Werner ◽  
Rüdiger Horstkorte ◽  
Dagobert Glanz ◽  
Karina Biskup ◽  
Véronique Blanchard ◽  
...  
Keyword(s):  
Sialic Acid ◽  
Culture Medium ◽  
Sialic Acids ◽  
Side Chain ◽  
Cell Culture Medium ◽  
Terminal Position ◽  
Human Erythropoietin ◽  
Recombinant Glycoproteins ◽  
Complex Glycans ◽  
Over Time

Abstract During the last years, the use of therapeutic glycoproteins has increased strikingly. Glycosylation of recombinant glycoproteins is of major importance in biotechnology, as the glycan composition of recombinant glycoproteins impacts their pharmacological properties. The terminal position of N-linked complex glycans in mammals is typically occupied by sialic acid. The presence of sialic acid is crucial for functionality and affects the half-life of glycoproteins. However, glycoproteins in the bloodstream become desialylated over time and are recognized by the asialoglycoprotein receptors via the exposed galactose and targeted for degradation. Non-natural sialic acid precursors can be used to engineer the glycosylation side chains by biochemically introducing new non-natural terminal sialic acids. Previously, we demonstrated that the physiological precursor of sialic acid (i.e., N-acetylmannosamine) can be substituted by the non-natural precursors N-propanoylmannosamine (ManNProp) or N-pentanoylmannosamine (ManNPent) by their simple application to the cell culture medium. Here, we analyzed the glycosylation of erythropoietin (EPO). By feeding cells with ManNProp or ManNPent, we were able to incorporate N-propanoyl or N-pentanoyl sialic acid in significant amounts into EPO. Using a degradation assay with sialidase, we observed a higher resistance of EPO to sialidase after incorporation of N-propanoyl or N-pentanoyl sialic acid.

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