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Record 15 of 161
Pentopyranosyl Oligonucleotide Systems. Part 11: Systems with Shortened Backbones: D)-beta-Ribopyranosyl-(4 yields 3 )- and (L)-alpha - Lyxopyranosyl-(4 yields 3 )-oligonucleotides
Author and Affiliation:
Wippo, Harald(Scripps Research Inst., Skaggs Inst. for Chemical Biology, La Jolla, CA, United States)
Reck, Folkert(Scripps Research Inst., Skaggs Inst. for Chemical Biology, La Jolla, CA, United States)
Kudick, Rene(Scripps Research Inst., Skaggs Inst. for Chemical Biology, La Jolla, CA, United States)
Ramaseshan, Mahesh(Eidgenoessische Technische Hochschule, Lab. of Organic Chemistry, Zurich, Switzerland)
Ceulemans, Griet(Scripps Research Inst., Skaggs Inst. for Chemical Biology, La Jolla, CA, United States)
Bolli, Martin(Scripps Research Inst., Skaggs Inst. for Chemical Biology, La Jolla, CA, United States)
Krishnamurthy, Ramanarayanan(Scripps Research Inst., Skaggs Inst. for Chemical Biology, La Jolla, CA, United States)
Eschenmoser, Albert(Scripps Research Inst., Skaggs Inst. for Chemical Biology, La Jolla, CA, United States)
Abstract: The (L)-a-lyxopyranosyl-(4'yields 3')-oligonucleotide system-a member of a pentopyranosyl oligonucleotide family containing a shortened backbone-is capable of cooperative base-pairing and of cross-pairing with DNA and RNA. In contrast, corresponding (D)-beta-ribopyransoyl-(4' yields 3')-oligonucleotides do not show base-pairing under similar conditions. We conclude that oligonucleotide systems can violate the six-bonds-per-backbone-unit rule by having five bonds instead, if their vicinally bound phosphodiester bridges can assume an antiperiplanar conformation. An additional structural feature that seems relevant to the cross-pairing capability of the (L)-a-lyxopyranosyl-(4' yields 3')-oligonucleotide system is its (small) backbone/basepair axes inclination. An inclination which is similar to that in B-DNA seems to be a prerequisite for an oligonucleotide system s capability to cross-pair with DNA.
Publication Date: Jan 01, 2001
Document ID:
20030067890
(Acquired Sep 23, 2003)
Subject Category: INORGANIC, ORGANIC AND PHYSICAL CHEMISTRY
Document Type: Journal Article
Publication Information: Bioorganic & Medicinal Chemistry (ISSN 0968-0896); 9; 2411-2428
Publisher Information: Elsevier Science Ltd., Unknown
Contract/Grant/Task Num: NAG5-4546
Financial Sponsor: NASA Goddard Space Flight Center; Greenbelt, MD, United States
Organization Source: Scripps Research Inst.; Skaggs Inst. for Chemical Biology; La Jolla, CA, United States
Description: 18p; In English
Distribution Limits: Unclassified; Publicly available; Unlimited
Rights: Copyright
NASA Terms: DEOXYRIBONUCLEIC ACID; RIBONUCLEIC ACIDS; OLIGOMERS; NUCLEOTIDES; ORGANIC CHEMISTRY; SYNTHESIS (CHEMISTRY); ESTERS; LIQUID CHROMATOGRAPHY; CHEMICAL BONDS
Availability Source: Other Sources
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