Disulfide containing molecules

Psammaplin A is a symmetrical bromotyrosine-derived disulfide dimer isolated from a marine sponge Psammalysilla, which exhibits in vitro antibacterial activity against methicillin-resistant Staphylococcus aureus (Figure 11.96). ° In order to find potent and structurally simplified analogs of psammaplin A that could be used as tools for SAR smdies, Nicolaou et al. undertook the combinatorial synthesis of a library of disulfide-containing molecules using a pool of 88 synthetic... 

Thiol modified HA is generally prepared by conjugation with a disulfide containing molecules such as cystamine or a 3,3 -dithiopropionic acid dihydrazide that is coupled to HA using EDC chemistry. Reduction of disulfide bonds by dithiothreitol yields the desired thiol derivative. The thiol derivatives of HA has been extensively used to develop... 

Figure 1.121 Sodium tetrathionate reacts with thiols to form reactive sulfenylthiosulfate intermediates. Another sulfhydryl-containing molecule may couple to this active group to create a disulfide linkage.

Figure 4.4 The reaction of DSP with amine-containing molecules yields amide bond crosslinks. The conjugates may be cleaved by reduction of the disulfide bond in the cross-bridge with DTT.

Figure 4.5 DTSSP can form crosslinks between two amine-containing molecules through amide linkages. The conjugates may be cleaved by disulfide reduction using DTT.

Figure 4.17 DPDPB is a sulfhydryl-reactive crosslinker that forms disulfide bonds with thiol-containing molecules. The conjugates may be disrupted using a disulfide reducing agent such as DTT.

Figure 5.2 SPDP can react with amine-containing molecules through its NHS ester end to form amide bonds. The pyridyl disulfide group then can be coupled to a sulfhydryl-containing molecule to create a cleavable disulfide bond.

Figure 5.3 SMPT can form crosslinks between an amine-containing molecule and a sulfhydryl-containing compound through amide and disulfide linkages, respectively. The hindered nature of the disulfide group provides better stability toward reduction and cleavage.

Figure 5.14 PDPH reacts with thiol-containing compounds through its pyridyl disulfide end to form reversible disulfide linkages. Its hydrazide end then may be subsequently conjugated with an aldehyde-containing molecule to form hydrazone bonds. Glycoproteins may be crosslinked using this approach after periodate activation to...

Figure 5.15 PDPH may be used to add a sulfhydryl group to an aldehyde-containing molecule. After reacting its hydrazide end with the aldehyde to form a hydrazone bond, the pyridyl disulfide may be reduced with DTT to create a free thiol.

Figure 5.23 SAND can be used to modify amine-containing molecules, and then photo-initiate crosslinking to another amine-containing molecule via a ring-expansion process. The conjugates may be disrupted by reduction of the cross-bridge disulfide with DTT.

Figure 7.26 Dendrimers made with a disulfide-containing core can be reduced to produce dendrons having free thiol groups for surface modification. Dative binding of these thiol-dendrons to gold or metallic surfaces can provide a high density of amine groups for coupling proteins or other molecules.

Two Molecules Conjugated with a Disulfide-Containing Cross-linking Agent... 

Figure 11.9 Biotin-HPDP reacts with sulfhydryl-containing molecules through its pyridyl disulfide group, forming reversible disulfide bonds. The biotin group may be released from modified molecules by reduction with DTT.

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