Synthesis of 3-guaninyl- and 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone nucleosides

Abdullah Saleh; John G. D'Angelo; Martha D. Morton; Jesse Quinn; Kendra Redden; Rafal W. Mielguz; Christopher Pavlik; Michael B. Smith

doi:10.1021/jo2004617

Synthesis of 3-guaninyl- and 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone nucleosides

Abdullah Saleh, John G. D'Angelo, Martha D. Morton, Jesse Quinn, Kendra Redden, Rafal W. Mielguz, Christopher Pavlik, Michael B. Smith

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

12 Scopus citations

Abstract

l- And d-glutamic acids, as well as trans-4-hydroxy-l-proline, are converted to the corresponding 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analog. The protecting group used to block the lactam nitrogen in key intermediates has a significant effect on the diastereoselectivity of the coupling reaction with adenine or guanine.

Original language	English (US)
Pages (from-to)	5574-5583
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	76
Issue number	14
DOIs	https://doi.org/10.1021/jo2004617
State	Published - Jul 15 2011
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jo2004617

Cite this

@article{8bb1749085df4a96830153dcdc6cdbde,

title = "Synthesis of 3-guaninyl- and 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone nucleosides",

abstract = "l- And d-glutamic acids, as well as trans-4-hydroxy-l-proline, are converted to the corresponding 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analog. The protecting group used to block the lactam nitrogen in key intermediates has a significant effect on the diastereoselectivity of the coupling reaction with adenine or guanine.",

author = "Abdullah Saleh and D'Angelo, {John G.} and Morton, {Martha D.} and Jesse Quinn and Kendra Redden and Mielguz, {Rafal W.} and Christopher Pavlik and Smith, {Michael B.}",

year = "2011",

month = jul,

day = "15",

doi = "10.1021/jo2004617",

language = "English (US)",

volume = "76",

pages = "5574--5583",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

T1 - Synthesis of 3-guaninyl- and 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone nucleosides

AU - Saleh, Abdullah

AU - D'Angelo, John G.

AU - Morton, Martha D.

AU - Quinn, Jesse

AU - Redden, Kendra

AU - Mielguz, Rafal W.

AU - Pavlik, Christopher

AU - Smith, Michael B.

PY - 2011/7/15

Y1 - 2011/7/15

N2 - l- And d-glutamic acids, as well as trans-4-hydroxy-l-proline, are converted to the corresponding 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analog. The protecting group used to block the lactam nitrogen in key intermediates has a significant effect on the diastereoselectivity of the coupling reaction with adenine or guanine.

AB - l- And d-glutamic acids, as well as trans-4-hydroxy-l-proline, are converted to the corresponding 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analog. The protecting group used to block the lactam nitrogen in key intermediates has a significant effect on the diastereoselectivity of the coupling reaction with adenine or guanine.

UR - http://www.scopus.com/inward/record.url?scp=79960179842&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79960179842&partnerID=8YFLogxK

U2 - 10.1021/jo2004617

DO - 10.1021/jo2004617

M3 - Article

C2 - 21619029

AN - SCOPUS:79960179842

SN - 0022-3263

VL - 76

SP - 5574

EP - 5583

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 14

ER -

Synthesis of 3-guaninyl- and 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone nucleosides

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this