Preparation of Sulfonic Acids from Unsaturated Compounds<sup>1</sup>

Showell, John S.; Russell, John R.; Swern, Daniel

doi:10.1021/jo01055a031

Cited by 59 publications

(12 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Orcinol was purchased from Chroma-Gesellschaft, Schmidt & Co. (Stuttgart-Untertiirkheim, Germany), Diazald® (p-toluenesulfonylmethylnitrosamide) from the Aldrich Chemical Co. (Milwaukee, Wl), and BCA (bicinchoninic acid) Protein Assay Reagent from Pierce Europe, Oud-Beijerland, the Netherlands. Methyl laurylsulfonate was prepared as described by Showell et al (33), using Diazald® as a source of diazomethane (24,26). P gingivalis OMZ309 (strain W83, from J. M. Hardie, London Hospital Medical College), S. artemidis OMZ317 (in-house isolate), and S. sobrinus OMZ176 (in-house isolate), recruited from the culture collection of the Institut fur orale Mikrobiologie und ailgemeine Immunoiogie, Zentrum flir Zahn-, Mund-und Kieferheilkunde der Universitat Ztirich, were maintained as previously described (31).…”

Section: Methodsmentioning

confidence: 99%

The inhibitory action of fatty acids on oral bacteria

Shapiro

1996

Oral Microbiology and Immunology

View full text Add to dashboard Cite

Saturated and unsaturated fatty acids and fatty acid derivatives were examined for their growth-inhibitory effects towards three selected oral bacteria: Porphyromonas gingivalis, Selenomonas artemidis, and Streptococcus sobrinus. Of the 45 compounds surveyed, only one, myristoleic acid, was inhibitory towards S. artemidis at a concentration < 100 micrograms/ml. cis-Hexadecenoic and cis-octadecenoic acids were generally inhibitory towards P. gingivalis and S. sobrinus, but there was no correlation between the position of the double bond and the minimum inhibitory concentration. Supra-minimum inhibitory concentrations of palmitoleic acid did not promote leakage of intracellular materials from either P. gingivalis or S. sobrinus, nor was L-isoleucine uptake by S. sobrinus inhibited. Fatty acids and derivatives were also examined for prospective synergistic or antagonistic interactions with thymol vis-à-vis growth inhibition of the test strains. Lauric acid and myristic acid each behaved synergistically with thymol to inhibit the growth of at least one test strain, whereas cis-10-heptadecenoic acid and thymol were noticeably antagonistic towards the growth of S. sobrinus.

show abstract

Section: Methodsmentioning

confidence: 99%

The inhibitory action of fatty acids on oral bacteria

Shapiro

1996

Oral Microbiology and Immunology

View full text Add to dashboard Cite

show abstract

“…The sample of methyl 1-octadecyl sulfonate was supplied by J. S. Showell of this Laboratory. Its preparation and properties have been described (7).…”

Section: Methodsmentioning

confidence: 99%

Infrared anisotropy and structure of crystalline methyl stearate and methyl octadecyl sulfonate

Susi

Jahn

1966

J Americ Oil Chem Soc

View full text Add to dashboard Cite

Infrared spectra of highly oriented crystalline films of methyl stearate and methyl 1-octadeeyl sulfonate have been obtained using polarized radiation with the electric vector parallel and at 45 ~ to crystallographic axes. The anisotropy of methyl stearate is in good agreement with the known structure and with vibrational assignments. The results obtained on the methyl ester of octadecyl sulfonic acid suggest a crystallographic plane (or glide plane) of symmetry. The hydrocarbon chains are tilted with respect to the end-group planes. The zigzag planes are roughly parallel to each other and perpendicular to the ac plane. Qualitative conclusions are drawn regarding the packing of the polar end-groups. Vibrational assignments are proposed for most prominent absorption bands.

show abstract

“…The 1 H NMR spectra further indicate that the radical addition of the different thiols to 7 proceeded in the expected anti-Markovnikov fashion. [46,[54][55][56][57][58][59] Markovnikov addition products should have produced a multiplet at 1.2-1.3 ppm due to the additional methyl groups and one or two quartets between 2.7-3.0 ppm due to additional methylene groups adjacent to the sulfur atoms, which are absent in the spectra in The results summarized in Table 2 provided the starting point for the post-modification of the longer oligomers 10 and 13. A first attempt to post-modify tetramer 10 with a 2.5-fold excess of thioglycolic acid only resulted in partial conversion of the double bonds (ca.…”

Section: Entrymentioning

confidence: 99%

A Post‐Modification Strategy for the Synthesis of Uniform, Hydrophilic/Hydrophobic Patterned α‐Hydroxy Acid Oligomers

2009

View full text Add to dashboard Cite

Hydrophilic/hydrophobic patterning is a well-established design strategy to guide secondary structure formation of both natural as well as non-natural oligomers and polymers. This contribution explores the feasibility of a new approach for the synthesis of uniform, sequence-defined, hydrophilic/ hydrophobic patterned oligo(α-hydroxy acid)s. The proposed strategy is based on post-modification of a reactive oligoester scaffold composed of an alternating sequence of hydrophobic [(2S)-2-hydroxy-4-methylpentanoic acid] and masked hydrophilic [(2S)-2-hydroxypent-4-enoic acid] α-hydroxy acids. The use of (2S)-2-hydroxypent-4-enoic acid instead of a complex side-chain-protected hydrophilic building block obvi-

show abstract

Preparation of Sulfonic Acids from Unsaturated Compounds¹

Cited by 59 publications

References 0 publications

The inhibitory action of fatty acids on oral bacteria

The inhibitory action of fatty acids on oral bacteria

Infrared anisotropy and structure of crystalline methyl stearate and methyl octadecyl sulfonate

A Post‐Modification Strategy for the Synthesis of Uniform, Hydrophilic/Hydrophobic Patterned α‐Hydroxy Acid Oligomers

Contact Info

Product

Resources

About

Preparation of Sulfonic Acids from Unsaturated Compounds1

Cited by 59 publications

References 0 publications

The inhibitory action of fatty acids on oral bacteria

The inhibitory action of fatty acids on oral bacteria

Infrared anisotropy and structure of crystalline methyl stearate and methyl octadecyl sulfonate

A Post‐Modification Strategy for the Synthesis of Uniform, Hydrophilic/Hydrophobic Patterned α‐Hydroxy Acid Oligomers

Contact Info

Product

Resources

About

Preparation of Sulfonic Acids from Unsaturated Compounds¹