3-deoxy Analog Research Articles

Nuclear magnetic resonance studies on wheat germ agglutinin-monomeric amino sugar interactions

The interaction of several N-acetyl- d-glucosamine analogs and of sialyl lactose with the lectin wheat germ agglutinin was studied by nuclear magnetic resonance. N- 2H 3-acetyl- d-gluocosamine was synthesized and found to displace the N-acetyl methyl signal toward its free chemical shift in N-acetylglucosamine and N-acetylneuraminic acid demonstrating common binding sites for the latter two compounds. The N-acetyl methyl signal of the α-methylglucoside of N-acetylglucosamine could be titrated but a 3-deoxy analog could not, the latter exhibiting very weak binding and demonstrating the importance of the 3-OH group in the binding process. Sialyl lactose (an N-acetylneuraminic acid analog) was rather tightly bound to the lectin. N-F 3-acetyl- d-glucosamine was synthesized and its binding to the lectin was studied at pH 4, 4.5, 5.1 by 19F NMR. The two anomers were found to bind with nearly equal K d ′s but exhibited a pH and anomer dependent Δ (total bound chemical shift). The -CF 3 analog was found to bind considerably stronger to the lectin than the -CH 3 compound. The clear resolution of the α and β anomers of this molecule make it a very useful probe of the lectin binding site.

Synthesis and biological action of 3-deoxy-vitamin D 3 and 3-deoxy-25-hydroxyvitamin D 3

Received 31 October 1978 1. Introduction 1,25(OH)2D3 is considered to be the active metab- olite of vitamin D, particularly in the intestine. This compound is produced in vivo from vitamin D by C-25 hydroxylation in the liver, followed by C-1 hydroxylation in the kidney. When 1,25(OH)2D3 interacts with intestinal cells, a specific CaBP is formed. The characteristic functional groups of 1,25(OH)2D3 are the Is, 313 and 25-hydroxy groups. Of these, only the 3/3-hydroxyl is present in the parent vitamin molecule. Therefore, the 2-step transformation of the active form raises the question of the significance of this hydroxy group for the intermediary metab- olism and the subsequent biological activity of the vitamin. Previous studies have shown however, that 3-deoxy analogues of 1,25(OH)2D3 are only slightly less potent biologically than the natural metabolite [1-3]. This paper reports the chemical synthesis of 3-deoxy-D3 and 3-deoxy-25(OH)D3 and their biolog- ical activity in chicks. The latter was evaluated by monitoring growth, plasma calcium, bone ash, duo- denal CaBP and the renal 25(OH)D3-1-hydroxyiase.

2. A novel approach for the total synthesis of 12-thiaequilenin and its 3-deoxy analogue

2. A novel approach for the total synthesis of 12-thiaequilenin and its 3-deoxy analogue

Vitamin D: 3-deoxy-lalpha-hydroxyvitamin D3, biologically active analog of lalpha-dihydroxyvitamin D3.

The ability of chemically synthesized 3-deoxy-lalpha-hydroxyvitamin D3, an analog of the biologically active form of vitamin D3, (lalpha,25-dihydroxyvitamin D3), to stimulate intestinal calcium transport was assessed. The 3-deoxy analog acted significantly more rapidly than vitamin D3 and only slightly slower than lalpha,25-dihydroxyvitamin D3. Comparison of the dose-response curves of these three vitamin D derivatives emphasizes the importance of the 3beta-hydroxyl group to biological activity.