By John S. Davies
Crucial reference resource for researchers within the pharmaceutical and allied industries, and on the biology/chemistry interface in academia. summary: necessary reference resource for researchers within the pharmaceutical and allied industries, and on the biology/chemistry interface in academia. learn more...
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Additional info for Amino Acids, Peptides and Proteins (SPR Amino Acids, Peptides, and Proteins (RSC)) (Vol 36)
Selenium analogues of sulfur containing amino acids have acquired increasing importance in the study of selenium poisoning and various detoxiﬁcation studies. 124 The easy conversion of tosylates into disulﬁdes and diselenides (Scheme 27) would be very useful in peptide synthesis where one can use Ser as a substitute for Cys avoiding the use of an additional protecting group and aerial oxidation of the sulfhydryl group. Scheme 27 Protection of thiol groups is sometimes troublesome. Conjugate, hetero-Michael addition of thiols to triple bonds activated by electron-withdrawing groups to aﬀord the one-to-one adduct is a well-known possibility, but it has limited scope.
180 The chiral carrier and transition metal were N-decyl-(L)-hydroxy-Pro and copper(II). A methodology for the enzymatic resolution of sterically constrained Ca-ﬂuoroalkyl substituted amino acids has been developed. Racemic H-(aTfm)Ala-NH2, H-(aCF2Cl)Ala-NH2 and H-(aCF2Br)Ala-NH2 were separated with very high enantioselectivity using amidase from Mycobacterium neoaurum, yielding the corresponding (R)-acids. 100 The enzyme BSL2, a highly active lipase, is used in the kinetic resolution of N-(2-ethyl-6-methylphenyl)alanine from the corresponding racemic methyl ester.
Scheme 29 Acid derivatives of phospholene oxides are a new class of compounds and expected to be possessing of potential biological activities. A convenient synthetic approach has been established to prepare a new class of 1-L-a-amino acid derivatives of phospholene oxides by amination of (Æ)-1-chloro-2-phospholene-1-oxides with several optically pure L-a-amino acid esters (Scheme 30). 134 Scheme 30 b-Phosphono Ala (AP3) and its derivatives are the P-analogues of Asp and are biologically important compounds, due to their antagonist activity on the central nervous system and their use in the synthesis of numerous enzyme inhibitors or modiﬁed peptides involved in viral maturation, cell development or infectivity.