1986
DOI: 10.7164/antibiotics.39.44
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K-26, a novel inhibitor of angiotensin I converting enzyme produced by an Actinomycete K-26.

Abstract: A novel inhibitor of angiotensin I converting enzyme (ACE), designated K-26, was isolated from the broth filtrate of an actiomycete K-26. K-26 is a water soluble, acidic peptide composed of an equal mol of L-isoleucine, L-tyrosine and l(R)-l-amino-2-(4-hydroxyphenyl)-ethylphosphonic acid. The IC50 of K-26 for ACE inhibition was 6.7 ng/ml when hippuryl-Lhistidyl-L-leucine was used as a substrate of ACE. K-26 possesses hypotensive activity in vivo.Angiotensin I converting enzyme (ACE) has been found to play a cr… Show more

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Cited by 53 publications
(30 citation statements)
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“…Hydrolysis of the C -terminal peptide linkage of dehydrophos would result in an enamine that is expected to hydrolyze to methyl acetylphosphonate, which is a structural analog of pyruvate and could inhibit pyruvate utilizing enzymes. On the other hand, the reactive vinyl phosphonate moiety in dehydrophos may inhibit a cellular process directly, analogous to the activity of the phosphonotripeptide K-26 (vide infra) that inhibits angiotensin converting enzyme without the requirement of hydrolysis (134). Future studies should shed light onto these questions.…”
Section: Dehydrophosmentioning
confidence: 99%
See 1 more Smart Citation
“…Hydrolysis of the C -terminal peptide linkage of dehydrophos would result in an enamine that is expected to hydrolyze to methyl acetylphosphonate, which is a structural analog of pyruvate and could inhibit pyruvate utilizing enzymes. On the other hand, the reactive vinyl phosphonate moiety in dehydrophos may inhibit a cellular process directly, analogous to the activity of the phosphonotripeptide K-26 (vide infra) that inhibits angiotensin converting enzyme without the requirement of hydrolysis (134). Future studies should shed light onto these questions.…”
Section: Dehydrophosmentioning
confidence: 99%
“…The compound is a potent inhibitor and shows promise in the treatment of high blood pressure (134). K-26 contains a phosphonate analog of tyrosine as its C-terminal residue that is shared in several analogs produced by Actinomadura strains (135, 136) (Figure 1).…”
Section: K-26mentioning
confidence: 99%
“…Fosfomycin (phosphonomycin) [19,8], bialaphos (SF-1293, phosphinothricin tripeptide, PTT) [1,41], phosalacine [45,46], trialaphos [28], dehydrophos (A53868) [24], FR-900098 [43], fosmidomycin [44], the plumbemycins [47,49,48], SF-2312 [60], and fosfonochlorin [58] were originally isolated by assaying inhibition of bacterial growth. Inhibition of fungal growth was used in isolation of the fosfazinomycins [18,42] and the rhizocticins [51], while inhibition of angiotensin converting enzyme (ACE) activity was used in discovery of I5B2 [29] and K-26 [65], and prevention of seed germination in the discovery of phosphonothrixin [33,57]. …”
Section: The Discovery Of Phosphonate Natural Product Antibioticsmentioning
confidence: 99%
“…1,2 Examples of naturally occurring phosphonates with established bioactivity include the industrially relevant herbicide phosphinothricin (PT); 3 antimalarials FR-900098 and fosmidomycin; 4 antimicrobials such as fosfomycin, 5 dehydrophos, 6 and the plumbemycins; 7 the antifungal rhizocticins; 8 and antihypertensive peptides K-4 9 and K-26. 10 …”
mentioning
confidence: 99%