Synthesis of cyclic dimeric methyl morpholinoside - A common synthetic precursor to cyclic dinucleotide analogs

Charles R. Kinzie; Andrew D. Steele; Stacy M. Pasciolla; William M. Wuest

doi:10.1016/j.tetlet.2014.07.038

Synthesis of cyclic dimeric methyl morpholinoside - A common synthetic precursor to cyclic dinucleotide analogs

Charles R. Kinzie, Andrew D. Steele, Stacy M. Pasciolla, William M. Wuest^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

An eight-step synthesis of cyclic dimeric methyl morpholinoside (c-di-MM), a common synthetic precursor to a number of cyclic dinucleotide analogs is reported. The synthesis of c-di-MM proceeds through a morpholine monomer prepared from readily available inexpensive starting materials and culminates with a key macrolactamization reaction to provide the macrocycle in 15% overall yield.

Original language	English
Pages (from-to)	4966-4968
Number of pages	3
Journal	Tetrahedron Letters
Volume	55
Issue number	35
DOIs	https://doi.org/10.1016/j.tetlet.2014.07.038
Publication status	Published - 2014
Externally published	Yes

Keywords

Morpholine
Second messenger molecule
Signaling nucleotide
c-di-AMP
c-di-GMP

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10.1016/j.tetlet.2014.07.038

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abstract = "An eight-step synthesis of cyclic dimeric methyl morpholinoside (c-di-MM), a common synthetic precursor to a number of cyclic dinucleotide analogs is reported. The synthesis of c-di-MM proceeds through a morpholine monomer prepared from readily available inexpensive starting materials and culminates with a key macrolactamization reaction to provide the macrocycle in 15% overall yield.",

keywords = "Morpholine, Second messenger molecule, Signaling nucleotide, c-di-AMP, c-di-GMP",

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AU - Kinzie, Charles R.

AU - Steele, Andrew D.

AU - Pasciolla, Stacy M.

AU - Wuest, William M.

PY - 2014

Y1 - 2014

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AB - An eight-step synthesis of cyclic dimeric methyl morpholinoside (c-di-MM), a common synthetic precursor to a number of cyclic dinucleotide analogs is reported. The synthesis of c-di-MM proceeds through a morpholine monomer prepared from readily available inexpensive starting materials and culminates with a key macrolactamization reaction to provide the macrocycle in 15% overall yield.

KW - Morpholine

KW - Second messenger molecule

KW - Signaling nucleotide

KW - c-di-AMP

KW - c-di-GMP

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U2 - 10.1016/j.tetlet.2014.07.038

DO - 10.1016/j.tetlet.2014.07.038

M3 - Article

AN - SCOPUS:84906069721

SN - 0040-4039

VL - 55

SP - 4966

EP - 4968

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 35

ER -

Synthesis of cyclic dimeric methyl morpholinoside - A common synthetic precursor to cyclic dinucleotide analogs

Abstract

Keywords

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