title: Reagents for bioorganic synthesis. 6. The design and synthesis of two novel polyfunctional organic reagents for biomacromolecular modification.
abstract: The design, synthesis, structure, and properties of two tetrafunctional organic reagents, namely, 2,2'-sulfonylbis[3-(carboxymethylamino)-(E,E)-N-(2-chloroeth yl)propenamide] (SBCCP) (1) and 2,2'-sulfonylbis[3-(carboxymethylamino)-(E,E)-N-(2-oxoeth yl)propenamide] (SBCOP) (2) are reported. Reagents 1 and 2 contain reactive bis(alkyl halide) and bis(aldehyde) functions, respectively, as well as bis(carboxylic acid) moieties. The reagents have potential applications for biomacromolecular cross-linking, in particular for the cross-linking of hemoglobin subunits. Single-crystal X-ray diffraction data of synthetic intermediates (4,5, and 12) provided information about structural features and tether lengths of the target reagents.
authors.affiliation: Department of Chemistry and Biochemistry, University of Maryland, Baltimore 21228.
authors.forename: C M
authors.initials: CM
authors.lastname: Bertha
authors.forename: S H
authors.initials: SH
authors.lastname: Hosmane
authors.forename: H
authors.initials: H
authors.lastname: Zhang
authors.forename: N S
authors.initials: NS
authors.lastname: Hosmane
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis; D003432:Cross-Linking Reagents / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D015195:Drug Design; D006454:Hemoglobins / Q000737:chemistry*; D007202:Indicators and Reagents; D046911:Macromolecular Substances; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013450:Sulfones / Q000138:chemical synthesis
chemical_list: C092907:2,2'-sulfonylbis(3-(carboxymethylamino)-N-(2-chloroethyl)propenamide); C092908:2,2'-sulfonylbis(3--(carboxymethylamino)-N-(2-oxoethyl)propenamide); D000447:Aldehydes; D003432:Cross-Linking Reagents; D006454:Hemoglobins; D007202:Indicators and Reagents; D046911:Macromolecular Substances; D013450:Sulfones