Microdegradation Procedure for Radioactive Peptide Ergot Alkaloids

Basmadjian, Garo P.; Floss, Heinz G.

doi:10.1002/jps.2600600636

Cited by 5 publications

(2 citation statements)

References 14 publications

(4 reference statements)

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“…The synthesis of aminoDAHP has been described . The N -(2,4-dinitrophenyl) derivative of aminoDAHP (DNP-aminoDAHP) was prepared following a procedure employed by Basmadjian and Floss …”

Section: Methodsmentioning

confidence: 99%

“…28 The N-(2,4dinitrophenyl) derivative of aminoDAHP (DNP-aminoDAHP) was prepared following a procedure employed by Basmadjian and Floss. 29 PEP, E4P, QA, SA, phenylmethanesulfonyl fluoride (PMSF), 2,4dinitrophenyl fluoride, and silylating reagent (SIGMA-SIL-A) were purchased from Sigma (St. Louis, MO). [amide- 15 N]Glutamine and 15 NH4Cl (98% 15 N) were obtained from Cambridge Isotope Laboratories.…”

Section: Methodsmentioning

confidence: 99%

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Biosynthesis of 3-Amino-5-hydroxybenzoic Acid, the Precursor of mC₇N Units in Ansamycin Antibiotics

et al. 1996

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The biosynthetic pathway of 3-amino-5-hydroxybenzoic acid (AHBA) formation was studied with cell-free extracts from the rifamycin B producer, Amycolatopsis mediterranei S699, and the ansatrienin A producer, Streptomyces collinus Tü1892. Phosphoenolpyruvate (PEP) plus erythrose 4-phosphate (E4P) gave AHBA in low but nevertheless significant (6%) yield. 3,4-Dideoxy-4-amino-d-arabino-heptulosonic acid 7-phosphate (aminoDAHP) was converted efficiently into AHBA (45%), as were 5-deoxy-5-amino-3-dehydroquinic acid (aminoDHQ, 41%) and 5-deoxy-5-amino-3-dehydroshikimic acid (aminoDHS, 95%). On the other hand, the normal shikimate pathway intermediate, 3-deoxy-d-arabino-heptulosonic acid 7-phosphate (DAHP) did not give rise to AHBA under these conditions. AminoDAHP (9%) was produced by incubation of [14C]PEP and E4P, but not of [14C]DAHP, with the cell-free extracts. The results demonstrate the operation of a new variant of the shikimate pathway in the formation of the mC7N units of ansamycin, and presumably also mitomycin, antibiotics which leads from PEP, E4P, and a nitrogen source directly to aminoDAHP and then via aminoDHQ and aminoDHS to AHBA.

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“…The synthesis of aminoDAHP has been described . The N -(2,4-dinitrophenyl) derivative of aminoDAHP (DNP-aminoDAHP) was prepared following a procedure employed by Basmadjian and Floss …”

Section: Methodsmentioning

confidence: 99%