2, 3-Diamino propionic acid

Diamino-propionic acid (DAPA) H2NCH2CH(NH2)C00H... 

Although the pK of the cy-amine group for Lys is within the titratable range and that for Arg would probably become so on coordination, the relatively long methylene chains render any tridentate chelation unlikely, and this appears to be the case.10- 4 The shorter methylene side chains in the synthetic diamine-monocarboxylates ornithine, 2,4-diaminobutanoic acid and 2,3-diamino-propionic acid lead to increased tridentate behaviour in that order. 

S -(4-Hydroxybenzyl)-glutathione (phenolic peptide) i.-a-Amino-y-oxalylaminobutyric acid (amino acid) I.-3-Oxalylamino-2-aminopropionic acid (= 3-JVOxalyl-2,3-diamino propionic acid (3-ODAP (3-Ar-Oxalylamino-L-alanine I.-BOAA)... 

Fig. 9 shows some examples, the list of which might be expanded almost arbitrarily. The only limitation hes in the reactivity of the aryl cuprates, which means that pyridyl or thienyl residues cannot be introduced yet. On the other hand the flexibility of the bisepoxide method is demonstrated by the synthesis of 2,3-diamino-propionic acid (p-amino-alanine) which is a constituent of antibiotic cyclo-peptides like tuberactinomycin A or, in form of the N-methyl derivative L-BMAA, occurs in the seeds of the local sago palm and had notoriously caused the Guam disease [8], with a certain kind of Alzheimer and Parkinson symptoms, until the American conquest of the island in World War II led to a change in nutrition (Fig. 10). 

Identification of the site of hydroxamate incorporation. To identify which amino acids were involved in the incorporation of hydroxylamine and the concomitant loss of the enzyme activity, all modified pepsins containing from 1.2 to 3.8 mole of hydroxamate per mole of pepsin (Table I) were subjected to Lossen rearrangement, followed by acid hydrolysis. All samples contained 2,3-diamino-propionic acid, but no 2,4-diaminobutyric acid was found using the amino acid analyzer. Thus, the PTFS-pepsin intermediates trapped with hydroxylamine must have been formed at the B-carboxyl groups of aspartate residues and glutamate residues were not involved. 

There is, of course, no paucity of examples using heteroatom-based nucleophiles. For example, aziridine-2-/-butyl carboxylate 102 reacts with primary amines to give the dialkylated diamino-propionic acid derivatives 103, which are interesting precursors for the synthesis of cyclosporin analogs. Again, attack occurs overwhelmingly at the B-carbon [95TL4955]. 

Consumption of seeds of the genus Lathyrus (Fabaceae) by man and his domestic animals produces a syndrome called lathyrism. Different amino acids produce the two forms of this malady neurolathyrism and osteolathyrism. 3-Aminopropionitrile 0-aminopropionitrile) (59) is the active osteolathyritic factor in Lathyrus species. Several factors are responsible for neurolathyrism. 3-Cyanoalanine (58), its 4-glutamyl derivative, 2,4-diaminobutyric acid (56), and the N-oxalyl derivative of 2,3-diaminopropionic (a,3-diamino-propionic) acid (57) are all known to be involved. These compounds are found primarily in plants of the genus iMth-yrus. 3-Cyanoalanine (58) and its 4-glutamyl derivative are also common in Vida species. Several related series of compounds are found in other members of the Fabaceae. 

Lathyrinogenic amino acids nonproteogenic amino acids occurring in the seeds of some species of vetch (Lathyrus). They include diaminobutyric acid H2N-(CH2)2-CH(NH2)- 00H (neurolathrinogenic effect), p-aminopropionitrile, which occurs as the glutamyl peptide in the seeds of Lathyrus. odoratus, and presumably the N-oxaloyl-a,p-diamino-propionic acid HOOC-CH(NH2)CH2-NH-CO-COOH. The disease caused in humans and animals by L.a.a. is called lathyrism, and takes various forms, e.g. neuro-(nerve)- and osteo(bone)-lathyrism e.g. PiAiy-gluta-rayI)aminopropionitrile causes skeletal abnormalities in rats... 

Figure 43 (a) Third generation peptide dendrimer ((Ac-His-Lys)8(Dap-His-Lys)4(Dap-His-Lys)2Dap-His-Lys-NH2) (Dap, diamino propionic acid) (b) Possible mechanisms for ester hydrolysis. 

All the library building blocks in this study are commercially available, with the exception of the diamino propionic acid Dp. This amino acid introduces an electron deficient aromatic ring that is absent from natural amino acids, and its Fmoc-protected form (the one needed for library synthesis) was prepared from commercially available A -benzyloxycarbonyl-L-asparagine (Fig. 3). 

Biosynthesis of Viomycin I. Origin of a,P-Diamino-propionic Acid and Serine. Biochemistry 13, 1221 (1974). 

The Maruoka group described an efficient enantioselective synthesis of optically active a-methyl serine derivatives by using their structurally simpHfied catalyst (S)-36b under mild phase-transfer conditions [107]. The asymmetric synthesis of a-alkyl cysteines, a-alkyl-a,p-diamino propionic acids, a-alkyl homoserines, and a-alkyl homocysteines was also carried out via the asymmetric phase-transfer catalytic a-alkylation of thiazoline-4-carboxylic acid tert-butyl esters 75, imidazoHne-4-carboxylic acid tert-butyl esters 76, and the six-membered ring substrates 77 and 78 [108]. 

Pyrimethamine Pyrimethamine, 2,4-diamino-5-(4 -chlorophenyl)-6-ethylpyrimidine (33.1.60), is synthesized from 4-chlorobenzycyanide, which upon condensation with methyl ester of propionic acid in the presence of sodium methoxide gives the 8-ketonitrile... 

Propionic acid, a-[ 2-[(a-carboxy-2-hydroxybenzyl)-imino]ethyl imino]-metal complexes, 788 Propionic acid, 2,3-diamino-metal complexes, 750... 

D Fouques, J Landry. Study of the conversion of asparagine and glutamine of proteins into diamino-propionic and diaminobutyric acids using [bis(trifluoroacetoxy)iodo]benzene prior to amino acid determination. Analyst 116 529-531, 1991. 

Verdini and coworkers [122] have introduced the 2-methyl-2-(2 -ni-tro)phenoxy-propionyl (Mnp) group for the preparation of stable monopro-tected gem-diamino alkyl residues 27 via IBTFA treatment of the carboxamide precursor 26. The precursor 26 is prepared by coupling amino a-carboxamide and 2-methyl-2-(2 -nitro)phenoxy-propionic acid as its O-succinimidyl ester 25. Hydrochloride salts, such as 27, are generally stable, crystalline compounds that can be stored at room temperature for several months. Once deprotonated, 27 is stable enough for acylation reactions (Scheme 9) [122]. 

A simple procedure for preparing 6-nitroimidazo[4,5-b]pyridine involves the action of formic acid on 2,3-diamino-5-nitropyridine. Similarly, when 3-amino-2-(0-diethylaminoethylamino)-S-nitropyridine (IX-210) is heated with formic acid (IX-211, R = H), the product is 3propionic acid (IX-211, R = Cj Hs), IX-212 (R = Cj Hj ) is obtained. ... 

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