Since the first attempts at the turn of the twentieth century, enormous progress has been made in the area of the chemical synthesis of O-glycosides. However, it was only in the past two decades that the scientific world had witnessed a dramatic improvement the methods used for chemical glycosylation. The development of new classes of glycosyl donors has not only allowed accessing novel types o...

Using the proton-proton nuclear Overhauser effect, a large number (150) of interproton distances, both intra- and internucleotide, are determined in solution for a non-self-complementary DNA undecamer comprising a portion of the specific target site for the cAMP receptor protein in the gal operon. It is shown that these distances are very similar to those expected for classical B DNA (RMS diffe...

In order to realize programmed build up of DNA objects, devices, and materials, a systematization of the principles at the basis of control of the assembly process is necessary. Thus far the discovery of fourstranded DNA architectures denominated Gquadruplexes was either serendipitous or through coincidental emergency. Here we utilize a rational approach for the design of G-quadruplexes based o...

The glycosidic bond torsion angles and the conformations of the two riboses of NAD’ bound to yeast and horse liver alcohol dehydrogenase in solution have been determined by a novel method involving the measurement of proton-proton transferred nuclear Overhauser enhancements by ‘H-nuclear magnetic resonance. In both cases the conformation of the-a8eirosine and nicotinamide ribose is 3’-endo of t...

In the title benzimidazolone, C(27)H(38)N(2)O(11), which has N-bound glycosidic units, all five-membered O-heterocyclic rings adopt envelope conformations [for the outer rings, the C atom with the dimethyl groups represents the flap atom]. The two glycosidic units are related by a non-crystallographic twofold rotation axis that passes through the carbonyl portion. In the mol-ecular structure, t...

In acidic media, the 5,6-double bond of uridine is rapidly hydrated to give a small amount of 6-hydroxy-5,6-dihydrouridine (Urd-H2O), the mechanism of which is known from studies of the acid-catalyzed dehydration of Urd-H2O (Prior, J. J., Maley, J., and Santi, D. V. (1984) J. Biol. Chem. 258, 2422-2428). In addition to dehydration, Urd-H2O also undergoes direct hydrolysis of the N-glycosidic bo...

The beta(1-->4) glycosidic linkage found in lactose is a prevalent structural motif in many carbohydrates and glycoconjugates. Using UV and IR ion-dip spectroscopies to probe benzyl lactoside isolated in the gas phase, we find that the disaccharide unit adopts only a single, rigid structure. Its fully resolved infrared ion-dip spectrum is in excellent agreement with that of the global minimum s...

Peptidoglycan is a giant molecule that forms the cell wall that surrounds bacterial cells. It is composed of alternating N-acetylglucosamine (NAG) and N-acetylmuramic acid (NAM) residues connected by β-(1,4)-glycosidic bonds and cross-linked with short polypeptide chains. Owing to the increasing antibiotic resistance against drugs targeting peptidoglycan synthesis, studies of enzymes involved i...