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Abstract: U-102408 has been isolated from S. arginensis cultures and fully characterized by NMR and MS. These studies indicate that U-102408 is identical with sulfomycin, and this data confirm the structure of sulfomycin which was assigned by chemical degradation and limited NMR studies. The biosynthetic origins of all U-102408 structural features have been elucidated through isotopic labeling experiments with primarily 13C but also using 14C, deuterium or tritium. Of particular interest, the 4-hydroxy-2-amino-2-penteno… Show more

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“…This requires the cleavage of glycine possibly with the formation of CO 2 , NH + 4 and 13 C-methylenetetrahydrofolate, as proposed in the biosynthesis of A10255 by Streptomyces gardneri . The observation that the methylene group of glycine is an effective source of methylating equivalents has also been made during the biosynthesis of the thiopeptide sulfomycin by Streptomyces arginensis (Fate et al, 1996). It is tempting to suggest that the enhancing effect of vitamin B12 on GE2270 antibiotic production can be explained by assuming that cobalamins act as coenzymes in one of these poorly studied reactions.…”
Section: Discussionmentioning
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rupbmjkragerfmgwileyiopcupepmcmbcthiemesagefrontiersapsiucrarxivemeralduhksmucshluniversity-of-gavle
“…This requires the cleavage of glycine possibly with the formation of CO 2 , NH + 4 and 13 C-methylenetetrahydrofolate, as proposed in the biosynthesis of A10255 by Streptomyces gardneri . The observation that the methylene group of glycine is an effective source of methylating equivalents has also been made during the biosynthesis of the thiopeptide sulfomycin by Streptomyces arginensis (Fate et al, 1996). It is tempting to suggest that the enhancing effect of vitamin B12 on GE2270 antibiotic production can be explained by assuming that cobalamins act as coenzymes in one of these poorly studied reactions.…”
Section: Discussionmentioning
“…The impossibility to obtain crystals for the vast majority of them prompted the assignment of their structure without a clear evidence of their stereochemistry. In spite of this limitation, in many cases their configuration has been proposed by analogy with similar isolates [ 38 , 39 ], via amino acid analysis [ 40 , 41 , 42 ] or via isotopic labeling through feeding with labeled amino acids [ 43 , 44 ]. In some cases, less conventional techniques have been chosen.…”
Section: Thiopeptidesmentioning
“…Both (Z ) and (E)forms occur in nature and are used for conscious peptide modification. The prototypical molecule not having a β-substituent is dehydroalanine ( Ala) and has been found in numerous members of the thiopeptide family of antibiotics [2,3]. Apart from this it serves in Michael addition with a range of amines and thiols, which provides an attractive route to the synthesis of natural and unnatural amino acid derivatives [4].…”
Section: Introductionmentioning