A preparation of N-Fmoc-N-methyl-α-amino acids and N-nosyl-N-methyl-α-amino acids

Amino Acids

Volumn 38, Issue 1, 2010, Pages 133-143

  Di Gioia, Maria Luisa ^a   Leggio, Antonella ^a   Liguori, Angelo ^a   Perri, Francesca ^a   Siciliano, Carlo ^a   Viscomi, Maria Caterina ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

Author keywords

Benzhydryl esters; Diazomethane; Diphenyldiazomethane; N Fmoc N methyl amino acid; N Methyl N nosyl amino acid; N Methylated dipeptides

Indexed keywords

AMINO ACID DERIVATIVE; PEPTIDE DERIVATIVE;

AMINO ACID ANALYSIS; AMINO ACID SYNTHESIS; ARTICLE; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN METHYLATION;

MOLECULAR STRUCTURE; PEPTIDES;

EID: 76449101367     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-008-0221-8     Document Type: Article

References (23)

1. AA Aboderin GR Delpierre JS Fruton 1965 Benzhydryl esters of amino acids in peptide synthesis J Am Chem Soc 87 5469 5472 10.1021/ja00951a039
2. F Arndt 1943 Diazomethane Org Synth Coll 2 165
3. L Aurelio RTC Brownlee AB Hughes 2004 Synthetic preparation of N-methyl-α-amino acids Chem Rev 104 5823 5846 10.1021/cr030024z (Pubitemid 40034047)
4. E Biron H Kessler 2005 Convenient synthesis of N-methylamino acids compatible with Fmoc solid-phase peptide synthesis J Org Chem 70 5183 5189 10.1021/jo050477z (Pubitemid 40863923)
5. E Biron J Chatterjee H Kessler 2006 Optimized selective N-methylation of peptides on solid support J Pept Sci 12 213 219 10.1002/psc.711 (Pubitemid 43349362)
6. ST Cheung NL Benoiton 1977 N-Methylamino acids in peptide synthesis. VII. Studies on the enantiomeric purity of N-methylamino acids prepared by various procedures Can J Chem 55 916 921 10.1139/v77-127
7. S De Bernardo JP Tengi GJ Sasso M Weigele 1985 Clavalanine (Ro 22-5417), a new clavam antibiotic from Streptomyces clavuligerus. 4. A stereorational synthesis J Org Chem 50 3457 3462 10.1021/jo00219a008 (Pubitemid 16243821)
8. ML Di Gioia A Leggio A Le Pera A Liguori A Napoli C Siciliano G Sindona 2003 "One-pot" methylation of N-nosyl-α-amino acid methyl esters with diazomethane and their coupling to prepare N-methyl dipeptides J Org Chem 68 7416 7421 10.1021/jo034233v
9. ML Di Gioia A Leggio A Liguori 2005 N-Methylation of peptides on selected positions during the elongation of the peptide chain in solution phase J Org Chem 70 3892 3897 10.1021/jo0478959
10. ML Di Gioia A Leggio A Liguori F Perri 2007 Solid-phase synthesis of N-nosyl and N-Fmoc-N-methyl-α-amino acids J Org Chem 72 3723 3728 10.1021/jo070075m 17439178 (Pubitemid 46762455)
11. RM Freidinger JS Hinkle DS Perlow BH Arison 1983 Synthesis of 9-fluorenylmethyloxycarbonyl-protected N-alkyl amino acids by reduction of oxazolidinones J Org Chem 48 77 81 10.1021/jo00149a016
12. Gilon C, Dechantsreiter MA, Burkhart F, Friedler A, Kessler H (2002) Synthesis of N-alkylated peptides. In: Goodman M, Felix A, Moroder L, Toniolo C (eds) Houben-Weyl methods of organic chemistry. Synthesis of peptides and peptidomimetics, vol E22c. Georg Thieme Verlag, Stuttgard, Germany (see also references cited therein)
13. K Kwang-Youn K Ji-Yeon 1999 Generation of diphenyldiazomethane by oxidation of benzophenone hydrazone with Magtrieve™ Bull Kor Chem Soc 20 771 772
14. RA Lee DS Donald 1997 Magtrieve™ an efficient, magnetically retrievable and recyclable oxidant Tetrahedron Lett 22 3857 3860 10.1016/S0040-4039(97)00771-5 (Pubitemid 27264679)
15. G Lowe T Vilaivan 1997 Dipeptides bearing nucleobases for the synthesis of novel peptide nucleic acids J Chem Soc, Perkin Trans 1 547 554 10.1039/a603699f (Pubitemid 127784798)
16. JR McDermott NL Benoiton 1973 N-Methylamino acids in peptide synthesis. III. Racemization during deprotection by saponification and acidolysis Can J Chem 51 2555 2561 10.1139/v73-385
17. SC Miller TS Scanlan 1997 Site-selective N-methylation of peptides on solid support J Am Chem Soc 119 2301 2302 10.1021/ja9635443 (Pubitemid 27160003)
18. SC Miller TS Scanlan 1998 oNBS-SPPS: a new method for solid-phase peptide synthesis J Am Chem Soc 120 2690 2691 10.1021/ja974252k (Pubitemid 28191692)
19. Schröder E, Lübke K (1965) The peptides. Methods of peptide synthesis, vol 1. Academic Press, New York
20. Stelakatos GC, Paganou A, Zervas L (1966) New methods in peptide synthesis. Part III. Protection of carboxyl group. J Chem Soc C:1191-1199. doi: 10.1039/j39660001191
21. S Torii H Tanaka M Taniguchi Y Kameyama M Sasaoka T Shiroi R Kikuki I Kawahara A Shimabayashi S Nagao 1991 Deprotection of carboxylic esters of β-lactam homologs. Cleavage of p-methoxybenzyl, diphenylmethyl, and tert-butyl esters effected by a phenolic matrix J Org Chem 56 3633 3637 10.1021/jo00011a034
22. S Zhang T Govender T Norström PI Arvidsson 2005 An improved synthesis of Fmoc-N-methyl-α-amino acids J Org Chem 70 6918 6920 10.1021/jo050916u (Pubitemid 41134390)
23. Wuts PGM, Greene TW (2007) Greene's protective groups in organic synthesis, 4th edn. Wiley, Hoboken