Amino acids and peptides. XIII. Synthetic studies on N-terminal tripeptide amide analogs of fibrin .ALPHA.-chain.

Kawasaki, Koichi; Tsuji, Toshiki; Hirase, Katsuhiko; Miyano, Masanori; Imoto, Yoshinori; Iwamoto, Masahiro

doi:10.1248/cpb.39.584

Cited by 6 publications

(3 citation statements)

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“…Literature methods for coupling N-alkylated amino acids (Scheme ) have used (i) the usual carbodiimide based coupling reagents, BOP, (ii) CF 3 NO 2 -PyBrOP, (iii) BEP and FEP, (iv) PyBroP, (v) active ester, and (vi) acid chloride method followed by N-methylation with diazomethane . Yields of 62− 99% and reaction times of 1−16 h were reported depending upon the Pg and −R group incorporated.…”

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confidence: 99%

Efficient Peptide Coupling Involving Sterically Hindered Amino Acids

et al. 2007

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Hindered amino acids have been introduced into peptide chains by coupling N-(Cbz- and Fmoc-alpha-aminoacyl)benzotriazoles with amino acids, wherein at least one of the components was sterically hindered, to provide compounds 3a-e, (3c +3 c'), 5a-d, (5a + 5a'), 6a-c, (6b + 6b'), 8a-c, 9a-e, 10a-d, and (10a + 10a') in isolated yields of 41-95% with complete retention of chirality as evidenced by NMR and HPLC analysis. The benzotriazole activation methodology is a new route for the synthesis of sterically hindered peptides. (Note: compound numbers written within brackets represent diastereomeric mixtures or racemates; compound numbers without brackets represent enantiomers.).

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Section: Resultsmentioning

confidence: 99%

Efficient Peptide Coupling Involving Sterically Hindered Amino Acids

et al. 2007

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“…While peptide synthesis using C -terminally unprotected N -methylamino acids is an attractive synthetic approach, such methods have not been thoroughly examined to date (Scheme ). Tantry and Babu have reported the use of a mixed anhydride and TMSCl as silylating agent, but the substrate scope was limited, with sarcosine (H-MeGly-OH) the only N -methylamino acid examined, and the product formed in moderate yield…”

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confidence: 99%

“…With these new activating reagents and reaction conditions in hand, a survey of the scope of various N -methylamino acids amenable for use as the nucleophile was conducted. We first tested H-MeGly-OH ( 2b ) to compare the reactivity of ISTABr to a previous report using IBCF . The reaction produced the corresponding dipeptide 3b in excellent yield (Figure .…”

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Isostearyl Mixed Anhydrides for the Preparation ofN-Methylated Peptides UsingC-Terminally UnprotectedN-Methylamino Acids

Kurasaki¹,

Nagaya

Kobayashi³

et al. 2020

Org. Lett.

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Sustainable and efficient manufacturing methods for N-methylated peptides remain underexplored despite growing interest in therapeutic N-methylated peptides within the pharmaceutical industry. A methodology for the coupling of C-terminally unprotected N-methylamino acids mediated by an isostearic acid halide (ISTAX) and silylating reagent has been developed. This approach allows for the coupling of a wide variety of amino acids and peptides in high yields under mild conditions without the need for a C-terminal deprotection step in the process of C-terminal elongation. These advantages make this a useful synthetic method for the production of peptide therapeutics and diagnostics containing N-methylamino acids.

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