Opening of the Ring of the Thiolactone of Homocysteine

Vigneaud, Vincent du; Patterson, Wilbur I.; Hunt, Madison

doi:10.1016/s0021-9258(18)73912-4

Cited by 42 publications

(10 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Comparing the 1 H NMR spectra of PGA and PGA-HC, the additional signals of the latter at 3.34 and 2.80 ppm can be respectively attributed to the hydrogens of two methylenes of thiolactone, 51 indicating the successful HC graing. As reported in the literature, 54 the homocysteine thiolactone is prone to ring opening between two molecules in solution, leading to a series of byproducts. So, a set of PGA-HC precursors (P50, P70, P90 and P120) with different HC feeding ratios (50%, 70%, 90% and 120%) were prepared in order to investigate the efficiencies of NCL reactions in this work.…”

Section: Synthesis Of Precursorsmentioning

confidence: 66%

“…However, excess feeding ratio of HC may also cause partial destruction of thiolactone in PGA-HC precursor's synthesis. 54 It may be the reason that leading a decrease of crosslinking points and resulting in a higher EWC value of 120P hydrogel than that of 90P hydrogel. Among all these samples, 90P-2 hydrogel showed the lowest EWC value of 3.2, which may be ascribed to its highest crosslinking density.…”

Section: Equilibrium Water Contentmentioning

confidence: 99%

“…It indicated that the crosslinking density was enhanced, resulting in a more compact hydrogel structure. However, excess feeding ratio of HC may also cause partial destruction of thiolactone in P120 precursor's synthesis, 54 which leading to a decrease of crosslinking points and resulting in a lower compressive strength of 120P-2 hydrogel. Among all these groups, 90P-2 showed the highest compressive strength, which is higher than that of 50P-2 by 19.5% (55.8 kPa vs. 46.7 kPa).…”

Section: 5 Mechanical Propertiesmentioning

confidence: 99%

See 2 more Smart Citations

Hybrid polypeptide hydrogels produced via native chemical ligation

Fan

Zhang

et al. 2015

RSC Adv.

View full text Add to dashboard Cite

show abstract

Section: Synthesis Of Precursorsmentioning

confidence: 66%

Section: Equilibrium Water Contentmentioning

confidence: 99%

Section: 5 Mechanical Propertiesmentioning

confidence: 99%

See 1 more Smart Citation

Hybrid polypeptide hydrogels produced via native chemical ligation

Fan

Zhang

et al. 2015

RSC Adv.

View full text Add to dashboard Cite

show abstract

“…HTL is susceptible to both nucleophilic and electrophilic attack because of its dual aminoacyl-thioester character. Self-condensation of two thiolactones (acylation of the free amino group of the one HTL molecule by the other HTL) can form the corresponding diketopiperazine derivative (3,6-bis(2-mercaptoethyl)piperazine-2,5-dione) [ 14 , 62 , 63 , 64 ]. Protecting of the amino group of thiolactone could maintain the integrity of the HTL ring.…”

Section: Resultsmentioning

confidence: 99%

Human Serum Albumin Labelling with a New BODIPY Dye Having a Large Stokes Shift

Raskolupova

Popova²,

Zakharova

et al. 2021

Molecules

View full text Add to dashboard Cite

BODIPY dyes are photostable neutral derivatives of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene. These are widely used as chemosensors, laser materials, and molecular probes. At the same time, BODIPY dyes have small or moderate Stokes shifts like most other fluorophores. Large Stokes shifts are preferred for fluorophores because of higher sensitivity of such probes and sensors. The new boron containing BODIPY dye was designed and synthesized. We succeeded to perform an annulation of pyrrole ring with coumarin heterocyclic system and achieved a remarkable difference in absorption and emission maximum of obtained fluorophore up to 100 nm. This BODIPY dye was equipped with linker arm and was functionalized with a maleimide residue specifically reactive towards thiol groups of proteins. BODIPY residue equipped with a suitable targeting protein core can be used as a suitable imaging probe and agent for Boron Neutron Capture Therapy (BNCT). As the most abundant protein with a variety of physiological functions, human serum albumin (HSA) has been used extensively for the delivery and improvement of therapeutic molecules. Thiolactone chemistry provides a powerful tool to prepare albumin-based multimodal constructions. The released sulfhydryl groups of the homocysteine functional handle in thiolactone modified HSA were labeled with BODIPY dye to prepare a labeled albumin-BODIPY dye conjugate confirmed by MALDI-TOF-MS, UV-vis, and fluorescent emission spectra. Cytotoxicity of the resulting conjugate was investigated. This study is the basis for a novel BODIPY dye-albumin theranostic for BNCT. The results provide further impetus to develop derivatives of HSA for delivery of boron to cancer cells.

show abstract

“…However, under alkali conditions, it is possible a hydrolysis side reaction and acylation of the amino group of one HTL by another HTL molecule most probably via an intermediate homocysteinyl-HTL with the formation of 2,5-diketopiperazine of Hcy (Figure 5) [47,57]. Upon oxidation of 2,5-diketopiperazine a disulfide polymer, as well as an aromatic compound, might result [45,57]. The presented reactions should keep in mind planning the synthesis procedures with HTL compound.…”

Section: Homocysteine Thiolactone Building Blocks As Potential Precursors For Materials and Probesmentioning

confidence: 99%

Homocysteine Thiolactone: Biology and Chemistry

Chubarov

2021

Encyclopedia

View full text Add to dashboard Cite

Homocysteine thiolactone is a five-membered cyclic thioester of amino acid homocysteine. It is generated from homocysteine as a result of an error-editing reaction, principally, of methionyl-tRNA synthetase. An elevated level of homocysteine thiolactone is associated with cardiovascular diseases, strokes, atherosclerosis, neurological abnormalities, etc., presumably because it reacts to the side chain of protein lysine causing protein damage and autoimmune responses. It is not only an important metabolite but also a versatile building block for organic and bioorganic synthesis. This entry contains data on the homocysteine thiolactone formation, metabolism, toxicity mechanism in vivo, and the bioorganic chemistry applications as a powerful synthetic tool in polymer science, sustainable materials development, and probes.

show abstract

Opening of the Ring of the Thiolactone of Homocysteine

Cited by 42 publications

References 6 publications

Hybrid polypeptide hydrogels produced via native chemical ligation

Hybrid polypeptide hydrogels produced via native chemical ligation

Human Serum Albumin Labelling with a New BODIPY Dye Having a Large Stokes Shift

Homocysteine Thiolactone: Biology and Chemistry

Contact Info

Product

Resources

About