.alpha.-Amino acids as chiral educts for asymmetric products. Chirospecific syntheses of methyl L-sibirosaminide and its C-3 epimer from L-allothreonine

Maurer, Peter; Knudsen, Christopher G.; Palkowitz, Alan D.; Rapoport, Henry

doi:10.1021/jo00203a008

Cited by 52 publications

(13 citation statements)

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“…Similarly, the original structure 36 of the sibirosamine moiety was revisited by detailed spectroscopic 47 analysis and further confirmed by the synthesis of L-sibirosamine. 48…”

Section: Activities Of Pyrrolobenzodiazepines Kmentioning

confidence: 99%

Biosynthesis, synthesis, and biological activities of pyrrolobenzodiazepines

Gerratana

2010

Medicinal Research Reviews

118

143

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Pyrrolobenzodiazepines (PBDs) are sequence selective DNA alkylating agents with remarkable antineoplastic activity. They are either naturally produced by actinomycetes or synthetically produced. The remarkable broad spectrum of activities of the naturally produced PBDs encouraged the synthesis of several PBDs, including dimeric and hybrid PBDs yielding to an improvement in the DNA binding sequence specificity and in the potency of this class of compounds. However, limitation in the chemical synthesis prevented the testing of one of the most potent PBDs, sibiromycin, a naturally produced glycosylated PBDs. Only recently the biosynthetic gene clusters for PBDs have been identified opening the doors to the production of glycosylated PBDs by mutasynthesis and biosynthetic engineering. The present review describes the recent studies on the biosynthesis of naturally produced pyrrolobenzodiazepines. In addition, it provides an overview on the isolation and characterization of naturally produced PBDs, on the chemical synthesis of PBDs, on the mechanism of DNA alkylation, and on the DNA binding affinity and cytotoxic properties of both naturally produced and synthetic pyrrolobenzodiazepines.

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“…Similarly, the original structure 36 of the sibirosamine moiety was revisited by detailed spectroscopic 47 analysis and further confirmed by the synthesis of L-sibirosamine. 48…”

Section: Activities Of Pyrrolobenzodiazepines Kmentioning

confidence: 99%

Biosynthesis, synthesis, and biological activities of pyrrolobenzodiazepines

Gerratana

2010

Medicinal Research Reviews

118

143

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“…As a rule, the use of -amino acids as starting materials require protection of the amine by a variety of groups: benzyloxy and methoxycarbonyl [3], phenylfluorenyl [4], phenylsulfonyl [5] etc. Other methods require transformation of the carboxylate function into other derivatives, such as acid halides, esters, amides, etc.…”

Section: -Amino Ketones From Enantiopure -Aminoacids or Their Derivatmentioning

confidence: 99%

“…Initially synthesis of the activated -amino ester was carried out by treatment of the N-Boc -amino acid with 2-chloro-4,6-dimethoxy [1,3,5] triazine in THF in the presence of morpholine (Scheme 9). Then, 1.0 equivalent of the Grignard derivative was added in the presence of CuI.…”

Section: Synthesis Of Non-functionalised -Amino Ketonesmentioning

confidence: 99%

Synthesis and Synthetic Applications of α-Amino Ketones Derived from Natural α-Amino Acids

Rodríguez‐Solla¹

2008

COC

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Enantiomerically pure -amino ketones are of great importance in natural product synthesis and pharmacological research. However no review concerning their synthesis and applications has been published. Therefore, this review is intended to highlight the above compounds, detailing the available methodologies to prepare enantiopure -amino ketones in the first part and some synthetic application in the second.

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“…Thiol "Click Chemistry", including thiol-ene, thiol-isocyanate, thiolhalogen and thiol-epoxy reactions, has attracted much attention in the last decade. 2 While the thiol-epoxy reaction has been applied widely, [3][4][5][6][7][8][9] the fundamental research has mainly focused on the efficiency of various base catalysts and the structure effects of thiols and epoxides. Inorganic bases like LiOH 10 have strong basicity, leading to high catalytic efficiency in the thiol-epoxy reaction.…”

mentioning

confidence: 99%

Kinetics based on the base-catalyzed mechanism of a click reaction between glycol dimercaptoacetate and glycidyl phenyl ether

Yao

Boen

et al. 2017

RSC Adv.

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.alpha.-Amino acids as chiral educts for asymmetric products. Chirospecific syntheses of methyl L-sibirosaminide and its C-3 epimer from L-allothreonine

Cited by 52 publications

References 0 publications

Biosynthesis, synthesis, and biological activities of pyrrolobenzodiazepines

Biosynthesis, synthesis, and biological activities of pyrrolobenzodiazepines

Synthesis and Synthetic Applications of α-Amino Ketones Derived from Natural α-Amino Acids

Kinetics based on the base-catalyzed mechanism of a click reaction between glycol dimercaptoacetate and glycidyl phenyl ether

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.alpha.-Amino acids as chiral educts for asymmetric products. Chirospecific syntheses of methyl L-sibirosaminide and its C-3 epimer from L-allothreonine

Cited by 52 publications

References 0 publications

Biosynthesis, synthesis, and biological activities of pyrrolobenzodiazepines

Biosynthesis, synthesis, and biological activities of pyrrolobenzodiazepines

Synthesis and Synthetic Applications of &#945;-Amino Ketones Derived from Natural &#945;-Amino Acids

Kinetics based on the base-catalyzed mechanism of a click reaction between glycol dimercaptoacetate and glycidyl phenyl ether

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Synthesis and Synthetic Applications of α-Amino Ketones Derived from Natural α-Amino Acids