2- Deoxy-scyllo-inosose

SteO08.22c AprC 384 17039 2-Deoxy-scyllo -inosose synthase,cyclase... 

In the interest of devising simple routes to starting materials commonly used in synthesis from sustainable resources, catechol has been made chemo-enzymatically in two steps from glucose in reasonable yield. 2-Deoxy-scyllo-inosose (171) was formed by incubation of D-glucose with recombinant 2-deoxy-scyl/o-inosose synthase and a hexokinase, and this material was reductively dehydrated to catechol by treatment with HI in acetic acid. ... 

Reagents i, Hexokinase ii, 2-deoxy-scyllo-inosose synthase iii, HI, HOAc... 

Cbl Cylitol pathway starting with 2-deoxy-scyllo inosose synthase... 

The General myo-lnositol and scyllo-Inosamine Pathway. Two distinct cyclitol pathways, which we earlier called Ca (started by myo-inositolphos-phate synthase) and Cb (started by T-deoxy-i cy/to-inosose synthase), are used in the initiation of AGA pathways. Here we will describe the Ca route and the Cb pathway in the paragraph on NEOs (see Section 2.2.2.1.3). The cyclitol pathway in the biosynthetic pathways for STRs, but also for other AGAs such as SPCs, KAS, and FORs and also the mixed type antibiotic HYG-A (see Section 2.2.4.3.1), starts with the formation of myo-inositol in a two-step pathway (Ca) that is not encoded in the itrAtt-clusters. The first step in streptidine biosynthesis (and any other myo-inositol utilising pathway) is the formation of a myo-inositol monophosphate (D-myo-inositol-3-phosphate or L-myo-inositol-1-phosphate) via L-myo-inositol-1-phosphate synthase, which in actinomycetes... 

D-glucose. This transformation has recently been demonstrated (32b), Synthesis in vitro is based on the work of Grosheintz and Fischer (S3). They found that 6-deoxy-6-nitro-D-glucose (or, likewise, 6-deoxy-6-nitro-L-idose) condensed in slightly alkaline solution to form two monodeoxymononitro-iiiositols. These were converted to the corresponding amines, one of which can also be obtained by reduction of the phenylhydrazone or oxime of mi/o-inosose-2 (scyllo-myo-inosose) h). The final and crucial step,... 

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