Amino Acids and Peptides (SPR Amino Acids, Peptides (RSC)) by J. H. Jones

By J. H. Jones

Expert Periodical stories offer systematic and precise evaluation assurance of development within the significant parts of chemical examine. Written through specialists of their expert fields the sequence creates a special carrier for the lively learn chemist, offering normal severe in-depth bills of growth specifically components of chemistry.

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E. reactions of side-chain functional groups), which amount to the conversion of one of the familiar aromatic or heterocyclic amino acids into others of the same class. DL-2-Carboxyphenylglycine itute) (noticed to be a potential glutamic acid subst- has been synthesized from phthalonic acid (g-HO2C. C6H4. coli. 12 Il-Substituted a - M n o Acids. a, in the synthesis of modified peptides. 8-Alkylation of furan-2-aldoxime by an a-halogeno-ester, followed either by acid hydrolysis or by reaction with hydroxylamine, yields an a-l-hydroxamino acid ((34) i ( 3 5 ) >.

32* However, the method involves distilling off water (from a mixture containing sodium hydroxide) and some DMF prior to adding the alkyl halide, and then the mixture is kept at 40°C for 2 hours before evaporation, so there seems to be considerable scope for racemization and side reactions. 32e The same process operates in the reaction of a chloro-imine with an N-alkoxycarbonylamino acid I ( 4 9 1 (50)i, previously thought t o lead to the N-pherlyl-1J-t\enzylainide. hy! si1yl ) 1 -L- hydroxyproline to give the cor responding 5-me thoxypyrroli di ne by electrolysis in MeOHI3=” a new route t o a-amino aldehydes through LiA1H4 reduction of a 2-amino acid 3,5-dimethylpyrazolide,33x corresponding CH&H&H=CH2.

In 25 Amino Acids 0 O NH ' *--ti M~ PhCH=CH O H COT OR R e a g e n t s : i , P h L i ; i i , N a N 3 ; iii,BoczO;iv,Sharpless oxidation,then TFA; v, H 2 / P t S c h e m e 12 y 3 6ocNH u i & CHO Me + epimer N-Boc -L- Ieuc in a l -+ vii (SSt S a t)-i n e H , H 6ui vi CONHPrn4 BocNH Reagents; i Me H OH ( R ) - 1 , 3 - d ; h y d r o x y p r o p a n e , TsOH, CH2C12/reflux; ii, T M S - C H Z C H = C H 2 / T i C l 4 ; v. c. l- C36cI-adeuosylhomacysteinelas and Syntheses of -methioninel-. - Hydroxylated bromobutanoic acid).

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