Design and Development of the First Peptide-Chelating Bisphosphane Bioconjugate from a Novel Functionalized Phosphorus(III) Hydride Synthon

Gali, Hariprasad; Karra, Srinivasa; Reddy, V. Sreenivasa; Katti, Kattesh V.

doi:10.1002/(sici)1521-3773(19990712)38:13/14<2020::aid-anie2020>3.3.co;2-i

Cited by 16 publications

(38 citation statements)

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“…Synthesis of peptide containing primary phosphine 23 demonstrate that the peptide conjugate 24 was formed in high yields with no modification of PH 2 groups. These results also confirm that the PH 2 groups of 18 and 19 are resistant to oxidation and are unreactive towards other functional groups in the peptides and the reagents used in SPPS [10]. The synthesis of such biomolecules which contain -PH 2 groups allows their conversion to hydrophilic alkyl phosphanes.…”

Section: Biomedical and Catalytic Implications Of Carboxylated Primarsupporting

confidence: 62%

“…5, shows the presence of unoxidized primary bisphosphine functionality. This figure exemplifies the diagnostic utility of the 31 P NMR spectroscopic technique to infer that the -PH 2 units are oxidatively inert even after subjecting the P 2 N 2 COOH primary phosphine precursor to harsh reaction conditions routinely used in the peptide synthesis [10,46].…”

Section: Phosphorus Nmr Spectroscopymentioning

confidence: 81%

“…This approach makes use of bromopropyl phosphine 17 as a key synthon obtained via the reduction of 3-bromopropyl phosphonate with dichloroaluminum hydride [10]. Reaction of bromopropyl phosphine 17 with the dianion of 6,8-dithiooctanoic acid produced the -COOH functionalized P 2 S 2 -primary bisphosphine framework 18 in >80% yields (Scheme 7) [10].…”

Section: Carboxylate Functionalized Primary Bisphosphinesmentioning

confidence: 99%

“…Reaction of bromopropyl phosphine 17 with the dianion of 6,8-dithiooctanoic acid produced the -COOH functionalized P 2 S 2 -primary bisphosphine framework 18 in >80% yields (Scheme 7) [10].…”

Section: Carboxylate Functionalized Primary Bisphosphinesmentioning

confidence: 99%

“…has been extensively utilized to produce a myriad of functionalized organophosphorus compounds [1,2]. Specifically, phosphorus-carbon functionalized compounds obtained via transformations across P-H bonds are versatile in various applications that include: (a) ligands for use in the development of catalytically useful tertiary phosphines [3][4][5][6][7][8], (b) chelating frameworks for use in the development of new chemotherapeutic and radioimaging agents in nuclear medicine [9][10][11], (c) precursors for applications in chemical vapor deposition (CVD) processes [12][13][14], and (d) chemical precursors or synthons of antimicrobial and bactericidal agents [15]. Primary phosphines (RPH 2 ), especially alkyl phosphines, are, in general, airsensitive compounds.…”

Section: Introductionmentioning

confidence: 99%

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New Vistas in Chemistry and Applications of Primary Phosphines

Katti¹,

Pillarsetty²,

Kannan³

2003

New Aspects in Phosphorus Chemistry III

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Primary phosphines (R-PH 2 ) are an important class of compounds in organophosphorus chemistry. Although discovered over a century ago, their chemistry and applications have gained prominence in recent years. This review discusses recent developments on synthesis, molecular structure, properties, and applications of primary phosphines. In particular, discussions on synthesis and properties emphasize recent results from our laboratory on the chemical architecture of amide, thioether, and carboxylate functionalized primary bisphosphines. The utility of bromo-and aminopropyl phosphines (X(CH 2 ) 3 PH 2 ; X=Br or NH 2 ) as building blocks to produce 'designer' primary phosphines that display exceptional oxidative stability is described. The review also discusses the utility of carboxylate functionalized primary phosphines for incorporation on to peptides and their potential applications in catalysis and biomedicine.

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Section: Biomedical and Catalytic Implications Of Carboxylated Primarsupporting

confidence: 62%

Section: Phosphorus Nmr Spectroscopymentioning

confidence: 81%

Section: Carboxylate Functionalized Primary Bisphosphinesmentioning

confidence: 99%

Section: Carboxylate Functionalized Primary Bisphosphinesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

New Vistas in Chemistry and Applications of Primary Phosphines

Katti¹,

Pillarsetty²,

Kannan³

2003

New Aspects in Phosphorus Chemistry III

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Synthesis and characterization of organometallic rhenium(І) and technetium(І) bile acid complexes

Huang

Zhu

et al. 2009

Journal of Organometallic Chemistry

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Phospha Derivatives of Tris(2-aminoethyl)amine (tren) and Tris(3-aminopropyl)amine (trpn): Synthesis and Complexation Studies with Group 4 Metals

et al. 2015

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The N,N′,N″-triphenyl-substituted derivative of tris(2-aminoethyl)phosphine (Ph 3 -phospha-tren, P-(CH 2 CH 2 NHR) 3 , R = Ph) and four derivatives of the related t r i s ( 3 -a m i n o p r o p y l ) p h o s p h i n e ( p h o s p h at r p n , P-(CH 2 CH 2 CH 2 NHR) 3 , R = i Pr, t Bu, Si t BuMe 2 , Ph) have been synthesized in addition to the parent phospha-trpn. Out of these ligand systems, only the N,N′,N″-triphenyl-substituted phosphatrpn derivative P(CH 2 CH 2 CH 2 NHPh) 3 was found to be suitable for coordination to group 4 metals. For titanium, zirconium, and hafnium, the C 3 -symmetric endo-P-configured dimethylamido complexes Ph [PN 3 ]M(NMe 2 ) of the former ligand have been prepared and converted into the corresponding triflates Ph [PN 3 ]M(OTf). Starting from these triflates, the benzyl complexes Ph [PN 3 ]M(Bn) (M = Ti, Zr, Hf) have been obtained via reaction with Bn 2 Mg(THF) 2 . In case of titanium, the benzyl species Ph [PN 3 ]Ti(Bn) is prone to thermal elimination of toluene, which results in the formation of a cyclometalated species. These findings are discussed in context with the very few group 4 trisamidophosphine complexes that have been reported earlier.

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Design and Development of the First Peptide-Chelating Bisphosphane Bioconjugate from a Novel Functionalized Phosphorus(III) Hydride Synthon

Cited by 16 publications

References 0 publications

New Vistas in Chemistry and Applications of Primary Phosphines

New Vistas in Chemistry and Applications of Primary Phosphines

Synthesis and characterization of organometallic rhenium(І) and technetium(І) bile acid complexes

Phospha Derivatives of Tris(2-aminoethyl)amine (tren) and Tris(3-aminopropyl)amine (trpn): Synthesis and Complexation Studies with Group 4 Metals

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