Enantiopure β3-amino acids-2,2-d2 via homologation of proteinogenic α-amino acids

Amino Acids

Volumn 32, Issue 3, 2007, Pages 401-404

  Caputo, R ^a   Longobardo, L ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

amino acid homologation; 3 amino acids; 3 amino nitriles d2; 2 aminoalcohols d2; 2 aminoiodides d 2; C 2 dideuterated amino acids

Indexed keywords

ALPHA AMINO ACID; AMINO ACID DERIVATIVE; BETA AMINO ACID; DEUTERIUM; AMINO ACID; AMINOALCOHOL; NITRILE;

AMINO ACID SYNTHESIS; ARTICLE; CHIRALITY; ENANTIOSELECTIVITY; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; AMINO ALCOHOLS; DEUTERIUM; NITRILES; STEREOISOMERISM;

EID: 34147170990     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-006-0384-0     Document Type: Article

References (16)

1. A Basak 1997 Enantioselective preparation of deuterated β-alanines E Juaristi Enantioselective synthesis of β-amino acids Wiley VCH New York 465 480
2. Bolognese A, Fierro O, Guarino D, Longobardo L, Caputo R (2006) One-pot synthesis of orthogonally protected enantiopure S-(aminoalkyl)-cysteine derivatives. Eur J Org Chem, 169-173
3. Brandl M, Kozhushkov SI, Zlatopolskiy BD, Alvermann P, Geers B, Zeeck A, de Meijere A (2005) The biosynthesis of 3-(trans-2-nitrocyclopropyl)alanine, a constituent of the signal metabolite hormaomycin. Eur J Org Chem, 123-135
4. R Caputo E Cassano L Longobardo G Palumbo 1995a Chiral N-protected β-iodoamines from α-aminoacids: a general synthesis Tetrahedron Lett 36 167 168
5. R Caputo E Cassano L Longobardo G Palumbo 1995b Synthesis of enantiopure N- and C-protected homo-β-amino acids by direct homologation of α-amino acids Tetrahedron 51 12337 12550
6. RP Cheng SH Gellman WF DeGrado 2001 β-Peptides: from structure to function Chem Rev 101 3219 3232
7. NJ Church DW Young 1998 Synthesis of the suicide substrate d-propargylglycine stereospecifically labelled with deuterium and investigation of its oxidation by d-amino acid oxidase J Chem Soc Perkin Trans 1 1475 1482
8. 1H-δ1 methyl) isoleucine into proteins for multidimensional NMR studies J Am Chem Soc 119 7599 7600
9. SP Gygi B Rist SA Gerber F Turecek MH Gelb R Aebersold 1999 Quantitative analysis of complex protein mixtures using isotope-coded affinity tags Nat Biotechnol 17 994 996
10. B Lygo LD Humphreys 2002 Enantioselective synthesis of α-carbon deuterium-labelled l-α-amino acids Tetrahedron Lett 43 6677 6679
11. JA Rufián-Henares FJ Morales 2006 Determination of acrylamide in potato chips by a reversed-phase LC-MS method based on a stable isotope dilution assay Food Chem 97 555 562
12. 2H-dephased REDOR J Am Chem Soc 122 12263 12269
13. SP Schrimpf V Meskenaite E Brunner D Rutishauser P Walther J Eng R Aebersold P Sonderegger 2005 Proteomic analysis of synaptosomes using isotope-coded affinity tags and mass spectrometry Proteomics 5 2531 2541
14. D Seebach A Beck DJ Bierbaum 2004 The world of β- and γ-peptides comprised of homologated proteinogenic amino acids and other components Chem Biodiv 1 1111 1239 and literature cited therein
15. Sewald N, Hiller KD, Helmreich B (1995) Asymmetric synthesis of β-amino acids and α-deuterated β-amino acids via conjugate addition of homochiral amidocuprates. Liebigs Ann, 925-928
16. T Stark H Justus T Hofmann 2006 Quantitative analysis of N-phenylpropenoyl-l-amino acids in roasted coffee and cocoa powder by means of a stable isotope dilution assay J Agric Food Chem 54 2859 2867