Amino acids and peptides. XVI. Synthesis of a tetrapeptide sequence (A9-A12) of glucagon

Costopanagiotis, Antigone; Handford, B. O.; Weinstein, Boris

doi:10.1021/jo01267a081

Cited by 16 publications

(5 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The residue was dissolved in methanol (2 ml) and 2hl-sodiurn ethyl hexanoate in methyl isobutyl ketone (0.03 ml) was added. The resulting solution was again evaporated and triturated with dry ether to afford the product disodium salt (26 mg, 44%) as an amorphous white solid; RF (a) 0.35; biochromatogram, single zone, RF 0.07; 6 [(CD3)2SO] 1.40 and 1.52 [6 H, 2s, (CH,),C], 1.69 (3 H, s, CH3CO), 2.18 [4 H, m, (CH2)2], 3.80 (1 H, s, 3-H of penicillin), 3.81 26 on a O.~-M scale to give the monoprotected acid, which was recrystallised from water (6.2 g, 30%); m.p. 214.5-216 "C (decomp.)…”

Section: N-acetyl-~-isog~utamyl-~-phenylglycyl-6-aminopenicillanicmentioning

confidence: 99%

Synthesis and biological activity of some fused β-lactam peptidoglycan analogues

Bentley¹,

Stachulski²

1983

J. Chem. Soc., Perkin Trans. 1

View full text Add to dashboard Cite

Section: N-acetyl-~-isog~utamyl-~-phenylglycyl-6-aminopenicillanicmentioning

confidence: 99%

Synthesis and biological activity of some fused β-lactam peptidoglycan analogues

Bentley¹,

Stachulski²

1983

J. Chem. Soc., Perkin Trans. 1

View full text Add to dashboard Cite

“…For crafting of models containing quinazolines and purines as the recognition units, 4-chloroquinazoline (Armarego 1961) was condensed with N=Z-Lys-OMe'HCI (Costopanagiotis et al 1968) in CH2CI 2 in the presence of Et3N to give quinazolyl…”

Section: Resultsmentioning

confidence: 99%

Synthetic nucleases crafted fromL-lysine

Ranganathan

Mishra

Patel

et al. 1994

Proc. Indian Acad. Sci. (Chem. Sci.)

View full text Add to dashboard Cite

A central strategy for the design of chemical nucleases is presented. This involves the utilization of the s-amino carboxylate unit of L-lysine to form Cu(II) templates to function as the cleaving centre on the one hand and co-amino group for the attachment of DNA recognition elements on the other, thus giving rise to a duplex recognition termini, harbouring a centrally placed Cu(II) for potentiation of oxidative scission. The recognition element studied encompasses a spectrum of structures ranging from quinazolines and purine residues to specifically crafted peptide segments that have potential to form secondary structures. These could be represented as R-K-Cu-K-R wherein R is the recognition system and K-Cu-K, a composite crafted from lysine, consisting of the cleaving centre from metal complexation of or-amino acid unit and the spacer consisting of the four methylene groups of the side chain. The binding and DNA scission profile of the sixteen chemical nucleases thus prepared and fully characterized have been probed by UV, fluorescence quenching and electrophoretic studies. Their binding to calf thymus DNA is associated with a decrease in s and an ~ 10-15 nm red shift. The involvement of GC sequence in binding is indicated from studies with poly[d(G-C)-d(G-C)] and poly[d(A-T).d(A-T)], wherein the hypochromicity and red shift were found to be quite pronounced in the former.Fluorescence quenching studies with Bz-Trp-Trp-K-Cu-K-Trp-Trp-Bz demonstrated the binding of one ligand at approximately every stretch of 112bp and approximately a stretch of 80 bp in the presence of salt. The DNA cleaving properties of all the nucleases were demonstrated with pBR 322 and p blue script 11KS using standard protocols. In all cases, covalently closed supercoiled (form I DNA) is converted largely into open circular (form II) suggesting nicking of the single strand at binding sites. Sequence specificity experiments with the nuclease. Bz-AIa-GIy-K-Cu-K-GIy-AIa-Bz in a 32p Y-end labeled 117 bp restriction fragment (Eco RI/Hind III) of pUC-18 showed almost exclusive attacks at thymidylate residues in particular, thymines corresponding to 5'T of the CTAT(3'-5') box. Whilst the most preferred site of attack is found at T of 3'-ATC-5' at the trinucleotide level, cleavage studies at low concentration have shown that at pentanucleotide level, the lone sequence 3'-GATCT-5' (a part of the inverted repeat -GAGATCTC-) is favoured (fragment 92) over the more frequently occurring Y-TATCT-5' segment.

show abstract

“…It was prepared according to Neuberger and Sanger (1943): mp 246-247.5°; [a]o + 14.2°( c 1, 2 n HC1); [a]?,3 +16.5°(c 2.93, CHCl2COOH); RFl 0.59; Rp1 0.49, 7?Fn0.61, RFV 0.04 [lit. (Neuberger and Sanger, 1943) [a]o +14.4°(c 1.6, 2 N HC1); (Costopanagiotis et al, 1968) [a]D +14°(c 1, 2 n HC1)].…”

Section: Synthesismentioning

confidence: 99%

Synthesis and conformational studies of model histones. Sequential and random polypeptides with the composition L-lysyl-L-alanyl-glycine

Cernosek¹,

Malin²,

Wells³

et al. 1974

Biochemistry

View full text Add to dashboard Cite

Amino acids and peptides. XVI. Synthesis of a tetrapeptide sequence (A9-A12) of glucagon

Cited by 16 publications

References 2 publications

Synthesis and biological activity of some fused β-lactam peptidoglycan analogues

Synthesis and biological activity of some fused β-lactam peptidoglycan analogues

Synthetic nucleases crafted fromL-lysine

Synthesis and conformational studies of model histones. Sequential and random polypeptides with the composition L-lysyl-L-alanyl-glycine

Contact Info

Product

Resources

About