Publication

Synthesis of 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives applying titanium-mediated reaction conditions

Pierre Vogel, Claudia Bello
2012
Journal paper
Abstract

The titanium-mediated cyclopropanation reaction using Ti((OPr)-Pr-i)(3)Me/EtMgBr/BF3 center dot OEt2 has been applied to various 2-cyanopyrrolidines for the synthesis of functionalized 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives (dideoxyiminoalditols). Under the same experimental conditions the trans-5-azidomethyl-2-cyanopyrrolidine derivative was not cyclopropanated but reduced into the corresponding 5-amino-2-cyano derivative. After polyol deprotection 2-(1-aminocyclopropyl)pyrrolidine-3,4-diols were obtained and their inhibitory activity towards 13 glycosidases has been evaluated. (2S,3S,4R,5S)-2-(1-Aminocyclopropyl)-5-methylpyrrolidine-3,4-diol (38), which has the same absolute configuration as L-fucose, is a moderate (IC50=44 mu M), but selective, inhibitor of alpha-L-fucosidase from human placenta. (C) 2011 Elsevier Ltd. All rights reserved.

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Related concepts (5)
Placenta
The placenta (: placentas or placentae) is a temporary embryonic and later fetal organ that begins developing from the blastocyst shortly after implantation. It plays critical roles in facilitating nutrient, gas and waste exchange between the physically separate maternal and fetal circulations, and is an important endocrine organ, producing hormones that regulate both maternal and fetal physiology during pregnancy. The placenta connects to the fetus via the umbilical cord, and on the opposite aspect to the maternal uterus in a species-dependent manner.
Placenta accreta spectrum
Placenta accreta occurs when all or part of the placenta attaches abnormally to the myometrium (the muscular layer of the uterine wall). Three grades of abnormal placental attachment are defined according to the depth of attachment and invasion into the muscular layers of the uterus: Accreta – chorionic villi attached to the myometrium, rather than being restricted within the decidua basalis. Increta – chorionic villi invaded into the myometrium. Percreta – chorionic villi invaded through the perimetrium (uterine serosa).
Development of the human body
Development of the human body is the process of growth to maturity. The process begins with fertilization, where an egg released from the ovary of a female is penetrated by a sperm cell from a male. The resulting zygote develops through mitosis and cell differentiation, and the resulting embryo then implants in the uterus, where the embryo continues development through a fetal stage until birth. Further growth and development continues after birth, and includes both physical and psychological development that is influenced by genetic, hormonal, environmental and other factors.
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Related publications (1)

New leads for selective inhibitors of alpha-L-fucosidases. Synthesis and glycosidase inhibitory activities of [(2R,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]furan derivatives

Pierre Vogel, Inmaculada Robina, Raynald Demange

Readily derived from D-glucose, 5-[(2R,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]-2-methyl-3-furoic esters and amides are selective and competitive inhibitors (K(i)greater than or equal to3 muM) Of alpha -L-fucosidase from bovine epididymis and from human placen ...
2001

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