Asymmetric synthesis of N-protected chiral 1-aminoalkylphosphonic acids and synthesis of side chain-functionalized depsiphosphonopeptides

Journal of Peptide Science

Volumn 12, Issue 5, 2006, Pages 337-340

  Liu, Han ^a   Cai, Shuzong ^a   Xu, Jiaxi ^a  

^a Peking University   (China)

Author keywords

Aminoalkylphosphonic acid; Asymmetric synthesis; Chlorophosphite; Depsiphosphonopeptide; Peptide; Phosphonopeptide

Indexed keywords

ALDEHYDE; CARBAMIC ACID; DEPSIPEPTIDE; PHOSPHITE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; CONTROLLED STUDY; MANNICH REACTION; PEPTIDE SYNTHESIS; PRIORITY JOURNAL;

ALDEHYDES; BENZOIC ACIDS; BENZYLAMINES; CARBAMATES; MODELS, CHEMICAL; PHOSPHITES; PHOSPHONIC ACIDS;

EID: 33646439560     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.731     Document Type: Article

References (20)

1. Kafarski P, Lejczak B. Synthesis of phosphono- and phosphinopeptides. In Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity, Kukhar VP, Hudson HR (eds.). John Wiley: Chichester, 2000.
2. Xu JX, Yu L. Synthesis of aminophosphonic acids and their eaters. Chin. J. Synth. Chem. 1999; 7: 153-158.
3. Xu JX, Ma Y, Duan LF. A novel synthetic route to N-protected 1-aminoalkylphosphonates. Heteroat. Chem. 2000; 11: 417-421.
4. Dai Q, Chen RY, Zhang CX, Liu Z. Synthesis of 2-[(benzyloxycarbonylamino) phenylmethyl]-1,3,2-benzodioxaphosphole 2- oxides. Synthesis 1998; 405-408.
5. Kumara Swamy KC, Kumaraswamy S, Senthil Kumar K, Muthiah C. Cyclic chlorophosphites as scaffolds for the one-pot synthesis of alfa-aminophosphonates under solvent-free conditions. Tetrahedron 2005; 46: 3347-3351.
6. Smith AB III, Yager KM, Taylor CM. Enantioselective synthesis of diverse alpha-aminophosphate diesters. J. Am. Chem. Soc. 1995; 117: 10879-10888.
7. Yuan CY, Wang GH. Studies on organophosphorus compounds; XLI. A convenient synthesis of alkyl hydrogen α-(benzyloxycarbonylamino) benzylphosphonates. Synthesis 1990; 256-258.
8. Dat Q, Chen RY. A facile synthesis of phenyl hydrogen α-(benzyloxycarbonylamino) benzylphosphonates. Synth. Commun. 1997; 27: 1653-1659.
9. Dai Q, Chen RY. A modified method for synthesis of alkyl hydrogen α-(benzyloxycarbonylamino)benzylphosphonates. Synth. Commun. 1997; 27: 3341-3347.
10. Xu JX, Fu NY. A facile synthesis of N-protected 1-aminoalkylphosphonamidate derivatives. Synth. Commun. 2000; 30: 4137-4145.
11. Xu JX, Fu NY. A novel and convenient method for synthesizing unsymmetrical N-benzyloxycarbonyl-protected 1-amino-1-aryl-alkylphosphonate mixed diesters. J. Chem. Soc. Perkin Trans. I 2001; 1223-1226.
12. Xu JX, Wei M. A convenient method for the synthesis of N-protected 1-aminoalkyl-phosphonate mixed monothioesters and dithioesters. Synth. Commun. 2001; 31: 1489-1497.
13. Liu H, Xu JX. Synthesis of 1-(N-ethoxycarbonylamino)alkylphosphonic monoesters. Amino Acids published online on July 28, 2005 DOI:10.1007/ s00726-005-0224-7.
14. 31P NMR spectroscopy. Heteroat. Chem. 2002; 13: 93-95.
15. Brunel JM, Pardigon O, Maffei M, Buono G. The use of (4R, 5R)- dicarbalkoxy-2-chloro-1,3,2-dioxaphospholanes as new chiral derivatizing agents for the determination of enantiomeric purity of alcohols by phosphorus-31 NMR. Tetrahedron: Asymmetry 1992; 3: 1243-1246.
16. Hoffmann M. A convenient synthesis of alkyl hydrogen 1-(benzyloxycarbonylamino)- alkanephosphonates. Synthesis 1986; 557-559.
17. Bartlett PA, Lamden LA. Inhibition of chymotrypsin by phosphonate and phosphonamidate peptide analogs. Bioorg. Chem. 1986; 14: 356-377.
18. Campagne JM, Coste J, Jouin P. (1H-Benzotriazol-1-yloxy)tris(di methylamino)phosphonium hexafluorophosphate- and (1H-benzotriazol-1-yloxy) tripyrrolidinophosphonium hexafluorophosphate-mediated activation of monophosphonate esters: Synthesis of mixed phosphonate diesters, the reactivity of the benzotriazolyl phosphonic esters vs the reactivity of the benzotriazolyl carboxylic esters. J. Org. Chem. 1995; 60: 5214-5223.
19. de Fatima Fernandez M, Vlaar CP, Fan H, Liu YH, Fronczek FR, Hammer RP. Synthesis of phosphonate and thiophosphonate esters and amides from hydrogen-phosphinates by a novel one-pot activation-coupling-oxidation procedure. J. Org. Chem. 1995; 60: 7390-7391.
20. Fu NY, Zhang QH, Duan LF, Xu JX. Facile synthesis of phosphonamidate and phosphonate-linked phosphonopeptides. J. Pept. Sci. 2005; in press, DOI:10.1002/psc.727.