A Reinvestigation of the Preparation of β-Methyl Lactoside<sup>1,2</sup>

Smith, F.; Cleve, J. W. Van

doi:10.1021/ja01128a010

Cited by 27 publications

(4 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Analysis of Rb samples by affinity chromatography on Sepharose 4B (Sigma) after extensive use and storage indicated that >85% of the Rb retained its ability to bind galactose during the course of our studies. Methyl /3-melibioside was synthesized from melibiose (Sigma Chemical Co.) using the method of Smith and Van Cleve (1952). Briefly, melibiose (5.0 g) was converted to the octaacetate(Na0Ac/Ac20,100°C,99%yield).…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Conformation of .beta.-methylmelibiose bound to the ricin B-chain as determined from transferred nuclear Overhauser effects

Bevilacqua¹,

Kim²,

Prestegard³

1992

Biochemistry

View full text Add to dashboard Cite

Transferred nuclear Overhauser effect (TRNOE) experiments have revealed a change in the torsion angles about the alpha-1-6 glycosidic bond of methyl beta-melibioside upon binding of the melibioside to the ricin B-chain (Rb). A full relaxation rate matrix simulation of experimental buildup curves aided in quantitative interpretation of 1D selective inversion recovery TRNOE experiments. The data are consistent with a model in which both major (omega approximately 170 degrees) and minor (omega approximately -60 degrees) conformers for methyl beta-melibioside are significantly populated in solution while the Rb/methyl beta-melibioside complex has little of the minor conformer populated. The results indicate that the ricin B-chain excludes binding of certain ligand conformations on the basis of unfavorable interactions between the protein surface and remote portions of the disaccharide system.

show abstract

Section: Methodsmentioning

confidence: 99%

“…Methyl j3-melibioside was synthesized from melibiose (Sigma Chemical Co.) using the method of Smith and Van Cleve (1952). Briefly, melibiose (5.0 g) was converted to the octaacetate (NaOAc/AczO, 100 OC, 99% yield).…”

Section: Melibiose Bound To Ricin B-chainmentioning

confidence: 99%

Conformation of .beta.-methylmelibiose bound to the ricin B-chain as determined from transferred nuclear Overhauser effects

Bevilacqua¹,

Kim²,

Prestegard³

1992

Biochemistry

View full text Add to dashboard Cite

show abstract

“…The fully protonated methyl /3-lactoside used in the experiments was prepared by the method of Smith and Van Cleve (1952). Briefly, 100 g of lactose was converted to the octaacetate.…”

Section: Methodsmentioning

confidence: 99%

Conformation of methyl .beta.-lactoside bound to the ricin B-chain: interpretation of transferred nuclear Overhauser effects facilitated by spin simulation and selective deuteration

Bevilacqua

Thomson²,

Prestegard³

1990

Biochemistry

View full text Add to dashboard Cite

Spin simulation and selective deuteration have been used to aid in the interpretation of 1D transferred nuclear Overhauser effect (TRNOE) NMR experiments on ricin B-chain/ligand systems. Application of these methods has revealed a change in the conformation of deuterated methyl beta-lactoside upon binding to the ricin B-chain which results in a slight change in glycosidic torsional angels which appear to dominate in the solution conformation. The combination of simulation and experiment also shows an important sensitivity of TRNOE magnitudes to dissociation rate constants and available spin-diffusion pathways for the ricin B-chain/ligand systems under study. The sensitivity to dissociation rates allows determination of rate constants for methyl beta-lactoside and methyl beta-galactoside of 50 and 300 s-1, respectively.

show abstract

“…Cellotetraose analogue was also synthesized from methyl b-D-lactoside. 29 Triflate 20 was obtained by conventional four steps [(i) p-methoxybenzylidene acetal formation, (ii) protection all of the remaining hydroxyl groups as PMP ethers, 25 Fig. 4).…”

Section: Syntheses Of Transition State Analoguesmentioning

confidence: 99%

Syntheses of cellotriose and cellotetraose analogues as transition state mimics for mechanistic studies of cellulases

Noguchi

Takemoto

Kidokoro

et al. 2011

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

A Reinvestigation of the Preparation of β-Methyl Lactoside^1,2

Cited by 27 publications

References 0 publications

Conformation of .beta.-methylmelibiose bound to the ricin B-chain as determined from transferred nuclear Overhauser effects

Conformation of .beta.-methylmelibiose bound to the ricin B-chain as determined from transferred nuclear Overhauser effects

Conformation of methyl .beta.-lactoside bound to the ricin B-chain: interpretation of transferred nuclear Overhauser effects facilitated by spin simulation and selective deuteration

Syntheses of cellotriose and cellotetraose analogues as transition state mimics for mechanistic studies of cellulases

Contact Info

Product

Resources

About

A Reinvestigation of the Preparation of β-Methyl Lactoside1,2

Cited by 27 publications

References 0 publications

Conformation of .beta.-methylmelibiose bound to the ricin B-chain as determined from transferred nuclear Overhauser effects

Conformation of .beta.-methylmelibiose bound to the ricin B-chain as determined from transferred nuclear Overhauser effects

Conformation of methyl .beta.-lactoside bound to the ricin B-chain: interpretation of transferred nuclear Overhauser effects facilitated by spin simulation and selective deuteration

Syntheses of cellotriose and cellotetraose analogues as transition state mimics for mechanistic studies of cellulases

Contact Info

Product

Resources

About

A Reinvestigation of the Preparation of β-Methyl Lactoside^1,2