Of streptamine

The first per-O-acetylated derivative to be studied131 was that (43) of streptamine, which gave, after deamination and acetylation, a crystalline N-acetyl-penta-O-acetyl derivative (44) (77% yield, before recrystallization), which was subsequently shown132 to be the product of inversion of configuration. The use of the di-O-acetyl derivative of the bis(acetamido) aminotetradeoxyinositol 45 improved133 the yield of substitution product isolated on deamination from less than 1% to 30%. 

Six moles of periodic acid were consumed per mole of streptamine with no formation of formaldehyde. - - Under comparable conditions, meso-inositol (m. p. 225°) was stated to consume six moles of periodic acid (formic acid was not detected or measured) and to give no formaldehyde while D-mannitol under like conditions consumed five moles of oxidant with the formation of two moles of formaldehyde. It is noteworthy that the periodic acid oxidation of the unsubstituted natural meso-inositol (see page 46) had been shown by Fleury, Poirot and Fievet to be anomalous (see page 51). 

Periodate oxidation studies on N,N -diacetylstreptamine, N,N -di-benzoylstreptamine (III) " and streptidine (VII) showed that each of these substances consumed only two moles of periodate. A 1,2 arrangement of the two amino or guanidino groups was therefore excluded since this would have required three moles of periodate. This conclusion was substantiated by the failure of streptamine to yield a cyclic ureide when treated with phosgene. ... 

The aromatization of streptamine by pyrolysis supported the evidence for the cyclic carbon skeleton, although it is to be noted that structural conclusions drawn from pyrolytic data are ordinarily open to question. Since the aromatization was achieved without elimination of nitrogen, the degradation also yielded information regarding the orientation of the nitrogen atoms. It was found that when hexaacetylstreptamine was heated in a sealed tube at 350 for one hour, 3.5 moles of acetic acid were produced and two crystalline products were obtained. One of the products was shown to be identical with 2,4-diacetamidophenol (X). ... 

Streptomycin appeared to enter Pseudomonas aeruginosa via active transport.59 In resistant Pseudomonas aeruginosa K102, reduced membrane permeability as well as decreased affinity of streptamine to the ribosome were plasmid-mediated.60 A 3"-deoxystreptomycin, active in vitro against streptomycin-resistant bacteria, was synthesized.61... 

At one time, there was much interest in using dibromotetrols for the synthesis of streptamine (107, R = H), and thence, streptomycin (151, G = guanidino). Reaction of certain dibromo tetraacetates (74 and 105) with ammonia in hot dioxane gives small yields of diaminotetrols, the configurations of which have not been fully established, but the products differ from natural streptamine. ... 

Other Substituted Tetrols. Cyclohexanetetrols having two additional unlike substituents are rare some of the derivatives or synthetic precursors of streptamine could be so classified. 

There have been many syntheses reported this year in quest of compounds with improved biological activity. Syntheses which involve glycosylation of streptamine derivatives have included the preparation of 4-0-(2-amino-2-deoxy-a-D-glucopyranosyl)- and 4-0-(6-amino-6-deoxy-a-D-glucopyranosyl)-2,5-dideoxystreptamine, the latter showing remarkable antimicrobial activity, ... 

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