3‐Hydroxypyrroles

and, Hamish Mcnab; Monahan, L. C.

doi:10.1002/9780470187340.ch4

Cited by 5 publications

(2 citation statements)

References 203 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…2A). Model N-alkylated 3-hydroxypyrroles are highly reactive, for example they can spontaneously form a dimer or add another aldehyde moiety through their C2 carbon [35]. (Aldehyde addition is the basis of the p-DIMAB colorimetric reaction product used to assay these cross-links in collagen [36]).…”

Section: Fibrillar Architecture and Cross-linking Of Bone Collagenmentioning

confidence: 99%

Bone Collagen: New Clues to Its Mineralization Mechanism from Recessive Osteogenesis Imperfecta

2013

View full text Add to dashboard Cite

Until 2006 the only mutations known to cause osteogenesis imperfecta (OI) were in the two genes coding for type I collagen chains. These dominant mutations affecting the expression or primary sequence of collagen α1(I) and α2(I) chains account for over 90% of OI cases. Since then a growing list of mutant genes causing the 5–10% of recessive cases has rapidly emerged. They include CRTAP, LEPRE1 and PPIB, which encode three proteins forming the prolyl 3-hydroxylase complex; PLOD2 and FKBP10, which encode respectively lysyl hydroxylase 2 and a foldase required for its activity in forming mature cross-links in bone collagen; SERPIN H1, which encodes the collagen chaperone HSP47; SERPIN F1, which encodes pigment epithelium-derived factor required for osteoid mineralization; and BMP1, which encodes the type I procollagen C-propeptidase. All cause fragile bone in infancy, which can include over-mineralization or under-mineralization defects as well as abnormal collagen post-translational modifications. Consistently both dominant and recessive variants lead to abnormal cross-linking chemistry in bone collagen. These recent discoveries strengthen the potential for a common pathogenic mechanism of misassembled collagen fibrils. Of the new genes identified, eight encode proteins required for collagen post-translational modification, chaperoning of newly synthesized collagen chains into native molecules or transport through the endoplasmic reticulum and Golgi for polymerization, cross-linking and mineralization. In reviewing these findings, we conclude that a common theme is emerging in the pathogenesis of brittle bone disease of mishandled collagen assembly with important insights on post-translational features of bone collagen that have evolved to optimize it as a biomineral template.

show abstract

Section: Fibrillar Architecture and Cross-linking Of Bone Collagenmentioning

confidence: 99%

Bone Collagen: New Clues to Its Mineralization Mechanism from Recessive Osteogenesis Imperfecta

2013

View full text Add to dashboard Cite

show abstract

“…Under flash vacuum pyrrolysis 46,47 (FVP) conditions (600°C, 0.005 Torr) bis-amino methylene derivatives of meldrum's acid (40) were transformed into mixtures of the pyrrolones 42 . FVP provides a simple and direct synthetic route to 1-substituted-3-hydroxypyrroles and their tautomers i.e.…”

Section: Synthesis Of Isomeric Pyrrolones By Flash Vacuum Pyrrolysis mentioning

confidence: 99%

2(3H)Pyrrolone – A Biologically Active Scaffold (A Review)

Ali¹,

Alama²,

Hamida³

et al. 2014

Orient. J. Chem

View full text Add to dashboard Cite

Construction of Vicinal Tetrasubstituted Stereogenic Centers via a Mannich‐Type Organocatalyzed Addition of Δ²‐Pyrrolin‐4‐ones to Isatin Imines

et al. 2018

View full text Add to dashboard Cite

Racemic D 2 -pyrrolin-4-ones (i. e. 4-pyrrolones), easily available in two steps from Nprotected a-amino acids, undergo organocatalysed asymmetric Mannich-type addition to isatin-derived ketimines to furnish the non-racemic oxindole-D 2pyrrolin-4-one adducts, stereoselectively (up to 96% ee, dr ! 15:1). The oxindole-pyrrolone products feature vicinal tetrasubstituted carbon stereocenters. The developed protocol has a broad substrate scope and tolerates diverse substituents at position C-5 in 4-pyrrolones and at positions N-1 and C-5/7 in isatin imines.

show abstract

3‐Hydroxypyrroles

Cited by 5 publications

References 203 publications

Bone Collagen: New Clues to Its Mineralization Mechanism from Recessive Osteogenesis Imperfecta

Bone Collagen: New Clues to Its Mineralization Mechanism from Recessive Osteogenesis Imperfecta

2(3H)Pyrrolone – A Biologically Active Scaffold (A Review)

Construction of Vicinal Tetrasubstituted Stereogenic Centers via a Mannich‐Type Organocatalyzed Addition of Δ²‐Pyrrolin‐4‐ones to Isatin Imines

Contact Info

Product

Resources

About

3‐Hydroxypyrroles

Cited by 5 publications

References 203 publications

Bone Collagen: New Clues to Its Mineralization Mechanism from Recessive Osteogenesis Imperfecta

Bone Collagen: New Clues to Its Mineralization Mechanism from Recessive Osteogenesis Imperfecta

2(3H)Pyrrolone – A Biologically Active Scaffold (A Review)

Construction of Vicinal Tetrasubstituted Stereogenic Centers via a Mannich‐Type Organocatalyzed Addition of Δ2‐Pyrrolin‐4‐ones to Isatin Imines

Contact Info

Product

Resources

About

Construction of Vicinal Tetrasubstituted Stereogenic Centers via a Mannich‐Type Organocatalyzed Addition of Δ²‐Pyrrolin‐4‐ones to Isatin Imines