5- Amino-4-hydroxypentanoic acid

Glutamic acid 1,5-Pentanediol, 2-amino-1,5-pentanediol, 4-amino-5-hydroxypentanoic acid, 4- amino-butanoic acid, 5- methyl-2-pyrrolidinone, 5 -hydroxynorvol ine, 5-(hydroxymethyl)-2-pyrrol idinone, pyroglutamic acid, 5-caprolactone Food additives, polymers, solvent Hermann, 2003 Feuchtenberger etal., 2005 Corma etal., 2007... 

The same group described the syntheses of some derivatives of 5-amino-5-deoxy-L-arabmonic acid, 5-amino-5-deoxy-D-xylonic acid, and (S)-5-amino-4-hydroxypentanoic acid, which wa-e paformed in sevraal steps from L-arabinose, D-xylose, and (S)-(-l-)-glutaniic acid, respectively [119], These monomers wctc polymerized to give methoxylated homo and copolyamides analogous to Nylon 5 [120, 121]. 

Amino-3-methyl-4-hydroxypentanoic acid lactone, Y"21.2 C6H11NO2S... 

Swern oxidation is a key step in the preparation of N-protected amino aldehydes. The N-protected amino aldehyde function is a key feature of intermediates en route to reduced-form peptides containing a CH2NH bond, e.g. (3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid (statine), and derivatives thereof, e.g. (3S,4S)-4-amino-5-cyclohexyl-3-hydroxypentanoic acid (cyclostatine), which, in turn, is an important intermediate for inhibitors of acidic protease such as renin. This process is accompanied by little racemization and gives products with excellent optical activities in excellent yields [1365]. 

N-Cbz statine 6.132). A number of other derivatives were prepared by this method, including 4-amino-3-hydroxypentanoic acid, 4-amino-3-hydroxy-7-melhyloctanoic acid, and 4-ammo-3-hydroxy-5-phenylpentanoic acid. 8... 

Another route to this cyclohexyl derivative involves the preparation of 6.183 via an olefmation reaction with a substituted phenylalinal derivative followed by reduction of the phenyl ring. The alcohol moiety in 6.183 was converted to the N-phthal-oyl derivative (6.184) by a Mitsunobu inversion.m Conjugate addition with a higher order silyl cuprate gave 6.185. The silyl moiety was converted to an alcohol (6.186) by treatment with tetrafluoroboric acid and then KF/m-chloroperoxy-benzoic acid. Removal of the phthalimidoyl group with hydrazine led to an amino-ester, which cyclized to lactam 5.757.11 Hydrolysis gave 4-amino-5-cyclohexyl-3-hydroxypentanoic acid (6.188) in 60% yield. 

Streptolidine (473), a guanidinoamino-acid that occurs as a component of the streptothricin group of antibiotics, has been synthesized by way of the lactam form (472) of (2S, 35,4i )-2,3,5-triamino-4-hydroxypentanoic acid (Scheme 154) 936 2R, 35, 45)-4-Amino-3-hydroxy-2-methyl-5-(pyrid-3-yl)pentanoic acid (474), a component of the antibiotic pyridomycin, has been derived from 3-deoxy-l,2 5,6-di-0-isopropylidene-3-C-methyl-a-D-allofuranose by the sequence of reactions outlined in Scheme 155. ... 

Example Synthesis of (2S,3R,4R)-2-Amino-4Kbenzyloxycarbonylamino)-3-hydroxypentanoic acid ammonium salt (Table 10.17, entry 10) [158]... 

Amino-5-hydroxypentanoic acid, A9.6 2-Amino-4-hydroxypentanoic acids, A 6.5, A 6.6 C3H N03S... 

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