Streptamine, structure

The obvious solution is to feed these cells with compounds that have structures similar to 2-deoxystreptamine, which would become incorporated into the neomycin. If for example, streptamine is included in the fermentation broth, this is incorporated into the neomycin produced. Thus ... 

Figure 1.2. The structural relationships of the streptamine family of antibiotics.

ANTIBIOTICS AMINOGLYCOSIDES. The term aminoglycoside is commonly used to refer to members of the class of antibacterial antibiotics, the structures of which are derived from n-streptamine (1. R=OH), r>-2-deoxystreptamine (I, R=H), or closely related compounds. The term aminocyclitoi is also sometimes used to identify this group of compounds. A typical member of this class, tobramycin, lias the structure (2),... 

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). ... 

The following structures represent the eight possible meso forms for streptamine. Since the compound is optically inactive, the two amino groups must lie on the same side of the ring. None of these eight possibilities has been eliminated. 

Treatment of N,N -dibenzoyldesoxystreptamine and N,N -dibenzoyl-streptamine under comparable conditions with periodate led to the consumption of one and two moles of periodate, respectively. These data were interpreted to show that the structure of the N,N -dibenzoyldesoxy-streptamine was LVII and thus the streptobiosamine portion in strepto-... 

In a similar investigation on the deoxy derivative (33) of iSr,Ar -dibenzoyl-streptamine, Folkers and coworkers isolated a crystalline dialdehyde compound which is, accordingly, 2,4-dibenzamido-2,4,5-trideoxy-a t/io-hexodialdose (34). The compound showed no aldehyde carbonyl absorption in its infrared spectrum and was, therefore, assigned a cyclic structure. It gave a crystalline bis(diethyl dithioacetal). 

Mass spectrometry has been used in structural studies of Gentamicin C and Sisomicin antibiotics. Gentamicin G was separated into three components (Cl, Cia, and C2) by column chromatography. Sugar analysis showed that Sisomycin and the three Gentamicins all contain 2-deoxy-streptamine (51), garosamine (52), and a 2,6-diamino-2,3,4,6-tetradeoxy-hexose (53) [unsaturated in Sisomicin (54)]. " °... 

Another related antibiotic, SS-56C, was reported by Inouye and colleagues. This antibiotic contains a streptamine residue instead of the 2-deoxystreptamine residue in A-396-I. From the culture broth of Streptomyces eurocidicus, n-mannosyl- and D-talosyl-2-deoxystreptamine were also isolated. In the structural studies, the mass spectra of their N-salicylidene derivatives were used. ... 

Paromamine, neamine, 4-0-(6-amino-6-deoxy- -D-glucopyranosyI)-2-deoxystreptamine, 5-0- (2-amino-2-deoxy-o-D-glucopyranosyl) -2-deoxy-streptamine, kasugamycin, and a,a-trehalosamine have been synthesized. A common feature in the structures of these antibiotics is the presence of an a-o-glycosidic linkage. In the total syntheses, modified Koenigs-Knorr reactions, or addition of nitrosyl chloride " to an enose, were successfully used. 

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