“Carba” peptide bond surrogates Different approaches to Gly‐Ψ(CH2‐CH2)‐d,l‐Xaa pseudo‐dipeptide units
- 1 March 1992
- journal article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 39 (3) , 273-277
- https://doi.org/10.1111/j.1399-3011.1992.tb00800.x
Abstract
Racemic “carba” pseudo-dipeptide units such as Gly-Ψ(CH2-CH2)-d,l-Xaa were obtained either through the Horner-Emmons condensation of N-tert.-butyloxycarbonyl-βalaninal with the appropriate substituted triethyl phosphonoacetate, or from commercially available 3-carbethoxy-2-piperidone.Keywords
This publication has 8 references indexed in Scilit:
- A general route to “carba” peptide bond replacements: Unequivocal synthesis of Boc--Phe-ψ(CH2-CH2)--Ala-OH and Boc--Phe-ψ(CH2-CH2)--Ala-OH.Tetrahedron Letters, 1990
- “Carba” peptide bond surrogates: synthesis of Boc--Leu-…(CH2-CH2)--Phe-OH and Boc-Leu-ψ-(CH2-CH2)--Phe-OH through a horner-emmons reaction.Tetrahedron Letters, 1990
- Pharmacological activity of cholecystokinin analogues modified in the Met28-Gly29 regionEuropean Journal of Pharmacology, 1990
- Probing peptide backbone function in bombesin. A reduced peptide bond analogue with potent and specific receptor antagonist activity.Journal of Biological Chemistry, 1988
- A Simple Method for tert-Butoxycarbonylation of Amides.Acta Chemica Scandinavica, 1986
- Wittig-Horner Reaction in Heterogeneous Media; V1. An Efficient Synthesis of α-Methylenecarboxylic Esters and α-Methyleneketones under Mild ConditionsSynthesis, 1984
- A mild two-step method for the hydrolysis of lactams and secondary amidesThe Journal of Organic Chemistry, 1983
- An Efficient Synthesis of Optically Active α-(t-Butoxycarbonylamino)-aldehydes from α-Amino AcidsSynthesis, 1983