858525-76-5Relevant academic research and scientific papers
Chemical synthesis of asparagine-linked archaeal N-glycan from Methanothermus fervidus
Sanapala, Someswara Rao,Kulkarni, Suvarn S.
supporting information, p. 3578 - 3583 (2014/04/03)
Several N-linked glycoproteins have been identified in archaea and there is growing evidence that the N-glycan is involved in survival and functioning of archaea in extreme conditions. Chemical synthesis of the archaeal N-glycans represents a crucial step
Efficient chemical synthesis of a dodecasaccharidyl lipomannan component of mycobacterial lipoarabinomannan
Fraser-Reid, Bert,Chaudhuri, Siddharfha Ray,Jayaprakash,Lu, Jun,Ramamurty, Changalvala V. S.
scheme or table, p. 9732 - 9743 (2009/04/06)
(Chemical Equation Presented) Lipomannan (LM) is one of the domains of lipoarabinomannan (LAM) glycolipids, the latter being one of several cell surface organic molecules that fortify mycobacterial species against external attack. Some members of mycobacterial families are pathogenic, most notably Mycobacterium tuberculosis and Mycobacterium leprae, while others are nonpathogenic, and used in the clinic, such as Mycobacterium smegmatis. Additional biological significance arises from the fact that LM has been implicated in several health disorders outside of those associated with mycobacterial pathogens, notably for treatment of bladder cancer. LM is comprised of a heavily lipidated phosphoinositide dimannoside headgroup, from which a mannan array, of varied complexity, extends. The latter consists of a 1,6-α-linked backbone flanked at position O2, not necessarily regularly, with α-linked mannosides. This paper gives an example of lipomannan synthesis in which all of the sugar components, whether functioning as donors or acceptors, are obtained from n-pentenyl orthoesters, themselves in turn prepared in three easy steps from D-mannose. Assembly of the mannan array is facilitated by the exquisite regioselectivity occasioned by the use of ytterbium triflate/N-iodosuccinimide as the trigger for reaction of n-pentenyl orthoesters.
Synthesis of a core arabinomannan oligosaccharide of Mycobacterium tuberculosis
Hoelemann, Alexandra,Stocker, Bridget L.,Seeberger, Peter H.
, p. 8071 - 8088 (2007/10/03)
The synthesis of a core arabinomannan (AM) oligosaccharide from Mycobacterium tuberculosis has been achieved using a convergent [6 + 6] glycosylation strategy and a defined set of building blocks. Dodecasaccharide 1, containing the key AM structural featu
