Beefy meaty peptide

Beefy meaty peptide

Names
Other names Delicious peptide; BMP; BMP (peptide); L-Lysylglycyl-L-α-aspartyl-L-α-glutamyl-L-α-glutamyl-L-seryl-L-leucyl-L-alanine; KGDEESLA
Identifiers
CAS Number	73984-05-1
ChemSpider	9269228
Jmol 3D model	Interactive image
PubChem	11094085
InChI InChI=1S/C34H57N9O16/c1-16(2)12-21(31(55)38-17(3)34(58)59)42-33(57)23(15-44)43-30(54)20(8-10-26(48)49)40-29(53)19(7-9-25(46)47)41-32(56)22(13-27(50)51)39-24(45)14-37-28(52)18(36)6-4-5-11-35/h16-23,44H,4-15,35-36H2,1-3H3,(H,37,52)(H,38,55)(H,39,45)(H,40,53)(H,41,56)(H,42,57)(H,43,54)(H,46,47)(H,48,49)(H,50,51)(H,58,59)/t17-,18-,19-,20-,21-,22-,23-/m0/s1 Key: JYGRAOYMDDFOSM-FQJIPJFPSA-N InChI=1/C34H57N9O16/c1-16(2)12-21(31(55)38-17(3)34(58)59)42-33(57)23(15-44)43-30(54)20(8-10-26(48)49)40-29(53)19(7-9-25(46)47)41-32(56)22(13-27(50)51)39-24(45)14-37-28(52)18(36)6-4-5-11-35/h16-23,44H,4-15,35-36H2,1-3H3,(H,37,52)(H,38,55)(H,39,45)(H,40,53)(H,41,56)(H,42,57)(H,43,54)(H,46,47)(H,48,49)(H,50,51)(H,58,59)/t17-,18-,19-,20-,21-,22-,23-/m0/s1 Key: JYGRAOYMDDFOSM-FQJIPJFPBN
SMILES CC(C)CC(C(=O)NC(C)C(=O)O)NC(=O)C(CO)NC(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(CC(=O)O)NC(=O)CNC(=O)C(CCCCN)N
Properties
Chemical formula	C34H57N9O16
Molar mass	847.88 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Beefy meaty peptide, also known as delicious peptide^[1] and abbreviated as BMP,^[2] is an 8-amino acid long peptide that has been identified as giving a beefy flavour to foods in which it is present. It was isolated from beef soup by Yamasaki and Maekawa.^[3] A research experiment was conducted by Wassenaar, Oord, and Schaaper in 1995 to evaluate the legitimacy of the alleged umami taste properties found within the octapeptide. However, biochemical analysis and conducted taste evaluations yielded the conclusion that the synthesized peptide did not exhibit any umami taste properties.^[4]

Sequence

Lys-Gly-Asp-Glu-Glu-Ser-Leu-Ala^[1]

References

1. Tamura, Masahiro; Nakatsuka, Tohru; Tada, Makoto; Kawasaki, Yoshihiro; Kikuchi, Eiichi; Okai, Hideo (1989). "The relationship between taste and primary structure of "delicious peptide" (Lys-Gly-Asp-Glu-Glu-Ser-Leu-Ala) from beef stew". Agricultural and Biological Chemistry 53 (2): 319. doi:10.1271/bbb1961.53.319.
2. Wang; Maga; Bechtel (1995). "Stability of Beefy Meaty Peptide to Pasteurization and SterilizationTemperatures". Lebensmittel-Wissenschaft und-Technologie 28 (5): 539. doi:10.1006/fstl.1995.0089.
3. Y. Yamasaki and K. Maekawa (1978). "A peptide with delicious taste". Agric. Biol. Chem. 42 (9): 1761. doi:10.1271/bbb1961.42.1761.
4. Pieter D. van Wassenaar, André H. A. van den Oord, and Wim M. M. Schaaper (1995). "Taste of "Delicious" Beefy Meaty Peptide". Journal of Agricultural and Food Chemistry 43 (11): 2828. doi:10.1021/jf00059a011.