156-86-5 Usage
Description
Homoarginine and 1-hydroxyhomoarginine were originally detected in significant concentration in the seeds of many Lathyrus species (Bell, 1962a,b; 1963). Homoarginine was isolated from the seeds of L. cicera (Bell, 1962b) and L. sativus (Rao et al., 1963). The hydroxy compound was obtained from the seeds of L. tingitanus (Bell, 1964). The comparative distribution of guanidino compounds in the seeds of two genus of the Papilionoideae, Lathyrus and Vicia, exhibits interesting features (Bell and Tirimanna, 1964). For example, the genus Lathyrus stores predominantly the C7 amino acids homoarginine, y-hydroxyhomoarginine and the related compound lathyrine, while the genus Vicia stores relatively high concentrations of canavanine and of the C6 amino acids arginine and y-hydroxyarginine. Apart from plants, homoarginine was found in small amounts in human body fluids ,. urine (Armstrong, 1967), serum (Matsumoto et al., 1976a) and cerebrospinal fluid (Mori et al., 1981b) and in mammalian brain (Mori et al., 1978, 1979 ). Increased urinary excretion was reported in hyperlysinemia (Armstrong and Robinow, 1967) and citrullinemia (Scott-Emuakpor et al., 19(2).
Homoarginine may be formed in mammals from lysine, by a homologous urea cycle in which arginine is replaced by lysine (Ryan and Wells, 1964; Scott-Emuakpor et al., 19(2). The excretion of homocitrulline and homoarginine in urine following administration of lysine to children supports this theory (Buergi et al., 1966). The biosynthesis of homoarginine has not been examined in plants, but y-hydroxyhomoarginine is synthesized from homoarginine in Lathyrus seeds (Bell, 1964). Subsequently both compounds have been identified as the precursors of the cyclic guanidino derivative, lathyrine, also present in Lathyrus seeds (Bell and Przybylska, 1965). Homoarginine and y-hydroxyhomoarginine probably serve as nitrogen reserves in Lathyrus seeds.
Inhibition of growth by homoarginine has been reported In various microorganisms (Walker, 1955; Rao et al., 1963).
gama-Hydroxyhomoarginine lactone isolated from the seeds of L. tingitanus (Bell, 1964) probably results from the cyclization of the open chain compound under acidic conditions.
Chemical Properties
White to off-white powder
Uses
Different sources of media describe the Uses of 156-86-5 differently. You can refer to the following data:
1. Homoarginine is an inhibitor of human arginase activity.
2. Homoarginine as marker for exogenous protein
Absorption and secretion of free homoarginine in the intestine: when 9 mmol homoarginine were infused into the proximal part of the jejunum, there was a 99.9% disappearance of the free amino acid homoarginine up to the ileum. In addition, following the infusion of 9 mmol homoarginine into the vena jugularis less than 0.2% of the infused homoarginine appeared in the intestine.
We concluded from these data that with the homoarginine method endogenous protein in the chyme of the intestine can be distinguished from the food protein as homoarginine is not incorporated into endogenous secreta and free homo arginine is completely absorbed.
Definition
ChEBI: An L-lysine derivative that is the L-enantiomer of homoarginine.
Check Digit Verification of cas no
The CAS Registry Mumber 156-86-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,5 and 6 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 156-86:
(5*1)+(4*5)+(3*6)+(2*8)+(1*6)=65
65 % 10 = 5
So 156-86-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H16N4O2/c8-5(6(12)13)3-1-2-4-11-7(9)10/h5H,1-4,8H2,(H,12,13)(H4,9,10,11)/t5-/m1/s1
156-86-5Relevant articles and documents
Structure assignment of lucentamycin e and revision of the olefin geometries of the marine-derived lucentamycins
Cha, Jin Wook,Park, Jin-Soo,Kwon, Hak Cheol,Sim, Taebo,Nam, Sang-Jip,Fenical, William,Del Valle, Juan R.
, p. 1648 - 1651,4 (2012)
A new lucentamycin analogue, lucentamycin E (5), was isolated from the culture broth of the marine-derived actinomycete Nocardiopsis lucentensis, strain CNR-712. The absolute stereostructure of 5 was assigned by comprehensive analyses of NMR data and by application of the advanced Marfey's method. The planar structure of 5 was analogous to lucentamycins A-D, whereas the olefin geometry of the 3-methyl-4-ethylideneproline moiety was found to be E, opposite of that previously reported. Consequently, a reinvestigation of the olefin geometries of the 3-methyl-4-ethylideneproline residues of lucentamycins A-D showed that the olefin geometries of the substituted proline functionalities must be revised to (2S,3R,E)-3-methyl-4-ethylideneproline.
Novel cyclic Hexapeptide LHRH antagonists
-
, (2008/06/13)
Novel peptides of the formula: STR1 where R 1 through R 8 are various radicals derived from L- and D- amino acids; having LHRH antagonist activity; useful in reducing fertility.Pharmaceutical compositions and methods for use in reducing fertility.
