43138-39-2Relevant academic research and scientific papers
Elongation of the side chain by linear alkyl groups increases the potency of salacinol, a potent α-glucosidase inhibitor from the Ayurvedic traditional medicine “Salacia,” against human intestinal maltase
Takashima, Katsuki,Sakano, Mika,Kinouchi, Eri,Nakamura, Shinya,Marumoto, Shinsuke,Ishikawa, Fumihiro,Ninomiya, Kiyofumi,Nakanishi, Isao,Morikawa, Toshio,Tanabe, Genzoh
supporting information, (2020/12/30)
Four chain-extended analogs (12a–12d) and two related de-O-sulfonated analogs (13a and 13c) by introducing alkyl groups (a: R = C3H7, b R = C6H13, c: R = C8H17, d: R = C10H2
Synthetic and Immunological Studies of Mycobacterial Lipoarabinomannan Oligosaccharides and Their Protein Conjugates
Wang, Lizhen,Feng, Shaojie,An, Lian,Gu, Guofeng,Guo, Zhongwu
, p. 10060 - 10075 (2015/11/03)
Lipoarabinomannan (LAM) is one of the major constituents of the Mycobacterium tuberculosis cell wall and an attractive molecular scaffold for antituberculosis drug and vaccine development. In this paper, a convergent strategy was developed for the synthes
Synthesis of carbohydrates in mineral-guided prebiotic cycles
Kim, Hyo-Joong,Ricardo, Alonso,Illangkoon, Heshan I.,Kim, Myong Jung,Carrigan, Matthew A.,Frye, Fabianne,Benner, Steven A.
experimental part, p. 9457 - 9468 (2011/08/04)
One present obstacle to the "RNA-first" model for the origin of life is an inability to generate reasonable "hands off" scenarios for the formation of carbohydrates under conditions where they might have survived for reasonable times once formed. Such scenarios would be especially compelling if they deliver pent(ul)oses, five-carbon sugars found in terran genetics, and exclude other carbohydrates (e.g., aldotetroses) that may also be able to function in genetic systems. Here, we provide detailed chemical analyses of carbohydrate premetabolism, showing how borate, molybdate, and calcium minerals guide the formation of tetroses (C4H8O4), heptoses (C7H14O7), and pentoses (C 5H10O5), including the ribose found in RNA, in "hands off" experiments, starting with formaldehyde and glycolaldehyde. These results show that pent(ul)oses would almost certainly have formed as stable borate complexes on the surface of an early Earth beneath a humid CO2 atmosphere suffering electrical discharge. While aldotetroses form extremely stable complexes with borate, they are not accessible by pathways plausible under the most likely early Earth scenarios. The stabilization by borate is not, however, absolute. Over longer times, material is expected to have passed from borate-bound pent(ul)oses to a branched heptulose, which is susceptible to Cannizzaro reduction to give dead end products. We show how this fate might be avoided using molybdate-catalyzed rearrangement of a branched pentose that is central to borate-moderated cycles that fix carbon from formaldehyde. Our emerging understanding of the nature of the early Earth, including the presence of hydrated rocks undergoing subduction to form felsic magmas in the early Hadean eon, may have made borate and molydate species available to prebiotic chemistry, despite the overall "reduced" state of the planet.
Synthesis of a bicyclic analogue of AZT restricted in an unusual O4′-endo conformation
Sorensen,Nielsen,Nielsen
, p. 4878 - 4886 (2007/10/03)
The [3.2.0]bicyclic β-nucleoside analogue 5 has been designed as a conformationally restricted analogue of the anti-HIV drug AZT. The synthesis of 5 as well as its α-anomer 29 is hereby described. The synthesis was accomplished from D-arabinose via a modified Corey-Link procedure stereo-selectively incorporating the azide moiety as well as a methyl ester function. When the tertbutyldiphenylsilyl group was used as a permanent protecting group, a selective formation of an oxetane ring failed. When using the p-methoxyphenyl group as a permanent protecting group, 5 and 29 were efficiently obtained via a selective reduction of the ester, a nucleobase coupling followed by separation of the anomers and ring-closing procedures. The nucleoside 5 is conformationally restricted in an unusual O4′-endo (East) conformation, which is an intermediate between the North- and South-type conformations. Nevertheless, neither 5 nor 29 displayed any anti-HIV activity.
Synthesis of pentaarabinofuranosyl structure motif A of Mycobacterium tuberculosis
Mereyala, Hari Babu,Hotha, Srinivas,Gurjar, Mukund K.
, p. 685 - 686 (2007/10/03)
The first synthesis of motif A, the branched chain arabinofuranosyl pentasaccharide [t-β-Araf-(1 → 2)-α-D-Araf]2-3,5-α-D-Araf-(1 → 5) which constitutes the major humoral immunological epitope in the arabinogalactan cell wall of Mycobacterium tu
Unusual 1,5-Hydride Shifts in Lewis Acid Mediated Reactions of Benzylated Sugars. Synthesis of 3-Alkylisochroman Derivatives
Martin, Olivier R.,Rao, S. P.,El-Shenawy, Hamdy A.,Kurz, Kenneth G.,Cutler, Amos B.
, p. 3287 - 3292 (2007/10/02)
Tin(IV) chloride mediated reactions of methyl 3,5-di-O-(4-chlorobenzyl)-2-O-(3-methoxybenzyl)-D-arabino- and -D-xylofuranosides 5 and 13 afforded unexpectedly, in one step, 3-alkyl-7-methoxyisochroman derivatives 7 and 14, respectively.These products are formed, most probably, by way of a complex process involving the intramolecular Friedel-Crafts alkylation of the activated benzyl group at O-2, leading to an internal aryl C-furanoside (e.g. 6), followed by an in situ reductive opening of the tetrahydrofuranyl ring of the intermediate C-furanoside.An experiment with a deuterium-labeled substrate demonstrated that this reductive step occurred by way of a stereospecific, tin(IV) chloride promoted 1,5 shift of a hydride ion from the 4-chlorobenzyl substituent at O-3 to the "anomeric" position of the C-furanoside, with retention of configuration at the migration terminus, and formation (after aqueous processing) of 4-chlorobenzaldehyde as a byproduct.This process provides a convenient methodology for the synthesis of enantiomerically pure isochroman derivatives from readily available carbohydrate precursors.
