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BAM-12P

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BAM-12P, a bovine adrenomedullary Met-enkephalin precursor, is isolated from bovine adrenal medulla.

Category

Others

Catalog number

BAT-015126

CAS number

75513-71-2

Molecular Formula

C62H97N21O16S

Molecular Weight

1424.63

Specification
Reference Reading

IUPAC Name

(2S)-2-[[(2S)-1-[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-methylbutanoyl]amino]acetyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]pentanedioic acid

Synonyms

H-Tyr-Gly-Gly-Phe-Met-Arg-Arg-Val-Gly-Arg-Pro-Glu-OH; L-tyrosyl-glycyl-glycyl-L-phenylalanyl-L-methionyl-L-arginyl-L-arginyl-L-valyl-glycyl-L-arginyl-L-prolyl-L-glutamic acid; N-[1-[N2-[N-[N-[N2-[N2-[N-[N-[N-(N-L-Tyrosylglycyl)glycyl]-L-phenylalanyl]-L-methionyl]-L-arginyl]-L-arginyl]-L-valyl]glycyl]-L-arginyl]-L-prolyl]-L-glutamic Acid; BAM 12; BAMD; Bovine Adrenal Medulla Dodecapeptide; 6,7-Arg-8-val-9-gly-10-arg-11-pro-12-glu-met-enkephalin; Methionine-enkephalin, arg(6,7)-val(8)-gly(9)-arg(10)-pro(11)-glu(12)-

Appearance

White Powder

Purity

≥95%

Density

1.5±0.1 g/cm3

Sequence

YGGFMRRVGRPE

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C62H97N21O16S/c1-34(2)50(57(96)75-33-48(87)76-42(15-9-26-72-62(68)69)58(97)83-27-10-16-45(83)56(95)81-43(59(98)99)21-22-49(88)89)82-54(93)40(14-8-25-71-61(66)67)79-52(91)39(13-7-24-70-60(64)65)78-53(92)41(23-28-100-3)80-55(94)44(30-35-11-5-4-6-12-35)77-47(86)32-73-46(85)31-74-51(90)38(63)29-36-17-19-37(84)20-18-36/h4-6,11-12,17-20,34,38-45,50,84H,7-10,13-16,21-33,63H2,1-3H3,(H,73,85)(H,74,90)(H,75,96)(H,76,87)(H,77,86)(H,78,92)(H,79,91)(H,80,94)(H,81,95)(H,82,93)(H,88,89)(H,98,99)(H4,64,65,70)(H4,66,67,71)(H4,68,69,72)/t38-,39-,40-,41-,42-,43-,44-,45-,50-/m0/s1

InChI Key

LNSYPNFYYCUMEW-ALRMXQJESA-N

Canonical SMILES

CC(C)C(C(=O)NCC(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(=O)NC(CCC(=O)O)C(=O)O)NC(=O)C(CCCN=C(N)N)NC(=O)C(CCCN=C(N)N)NC(=O)C(CCSC)NC(=O)C(CC2=CC=CC=C2)NC(=O)CNC(=O)CNC(=O)C(CC3=CC=C(C=C3)O)N

2. [Spatial structure of BAM-12P dodecapeptide and its analogues]

N A Akhmedov, Z G Tagiev, E M Gasanov, T A Makhmudova Bioorg Khim. 2005 May-Jun;31(3):245-50. doi: 10.1007/s11171-005-0030-8.

Theoretical conformational analysis was used to study the spatial structure and conformational properties of the bovine adrenal medulla dodecapeptide BAM-12P (Tyr1-Gly2-Gly3-Phe4-Met5-Arg6-Arg7-Val8-Gly9-Arg10-Pro11-Glu12). Twenty-three low-energy conformations of the BAM-12P backbone were shown to represent the spatial structure of the peptide. The inverse structural problem was solved, and synthetic analogues of BAM-12P were proposed, the spatial structures of which correspond to a set of low-energy potentially physiologically active conformations of the natural dodecapeptide. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2005, vol. 31, no. 3; see also http://www.maik.ru.

3. Molecular forms of the putative enkephalin precursor BAM-12P in bovine adrenal, pituitary, and hypothalamus

A Baird, N Ling, P Böhlen, R Benoit, R Klepper, R Guillemin Proc Natl Acad Sci U S A. 1982 Mar;79(6):2023-5. doi: 10.1073/pnas.79.6.2023.

A highly specific radioimmunoassay for one of the putative adrenomedullary [Met]enkephalin precursors, BAM-12P (Tyr-Gly-Gly-Phe-Met-Arg-Arg-Val-Gly-Arg-Pro-Glu-OH), has been developed. The BAM-12P antibodies recognize the COOH-terminal fragment of the peptide from Arg7 to Glu12 and do not crossreact with [Met5]- or [Leu5]enkephalin or any of their COOH-terminal lysine or arginine extended analogs. Specificity for the COOH-terminal Glu-OH is suggested by the 100% crossreactivity with BAM-12P5-12 and 0.3% crossreactivity with BAM-12P5-12 amide. Using these antibodies, we have measured three forms of BAM-12P-like immunoreactivity in extracts of bovine adrenal medulla, of which the major form (greater than 90%) corresponds to BAM-12P by molecular weight. Extracts of bovine adrenal cortex contain 1% the amount of a BAM-12P-like material (Mr approximately 1400; 20 ng per gland), possibly due to crosscontamination with adrenomedullary tissue. The major form of BAM-12P-like material in extracts of bovine neurointermediate pituitaries is of higher molecular weight than authentic BAM-12P (Mr approximately 4000); the remaining material (10%) corresponds to BAM-12P by molecular weight. There is no detectable BAM-12P-like immunoreactivity in crude or purified extracts of bovine anterior pituitaries. Extracts of bovine hypothalamic tissues contain small amounts of BAM-12P immunoreactivity (approximately 2 ng per fragment) which can be detected as one molecular form corresponding to a 1400-dalton molecule. The results indicate that the enkephalin precursor found in the adrenal medulla also may be present in the pituitary and hypothalamus. Furthermore, the processing of this molecule appears to be tissue-specific.