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SML0299

Sigma-Aldrich

Biphalin trifluoroacetate salt

≥97% (HPLC)

Synonym(s):

1,2-Bis(L-Tyr-D-Ala-Gly-L-Phe-)hydrazine, L-Tyrosyl-D-alanylglycyl-L-phenylalanine 2-(L-tyrosyl-D-alanylglycyl-L-phenylalanyl)hydrazide

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$226.00

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About This Item

Empirical Formula (Hill Notation):
C46H56N10O10 · xC2HF3O2
CAS Number:
126872-95-5
Molecular Weight:
909.00 (free base basis)
MDL number:
MFCD23380198
UNSPSC Code:
12352200
PubChem Substance ID:
329825305
NACRES:
NA.77

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Quality Level

100

assay

≥97% (HPLC)

form

lyophilized solid

color

white to beige

shipped in

wet ice

storage temp.

−20°C

SMILES string

OC(=O)C(F)(F)F.C[C@@H](NC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)NCC(=O)N[C@@H](Cc2ccccc2)C(=O)NNC(=O)[C@H](Cc3ccccc3)NC(=O)CNC(=O)[C@@H](C)NC(=O)[C@@H](N)Cc4ccc(O)cc4

InChI

1S/C46H56N10O10.C2HF3O2/c1-27(51-43(63)35(47)21-31-13-17-33(57)18-14-31)41(61)49-25-39(59)53-37(23-29-9-5-3-6-10-29)45(65)55-56-46(66)38(24-30-11-7-4-8-12-30)54-40(60)26-50-42(62)28(2)52-44(64)36(48)22-32-15-19-34(58)20-16-32;3-2(4,5)1(6)7/h3-20,27-28,35-38,57-58H,21-26,47-48H2,1-2H3,(H,49,61)(H,50,62)(H,51,63)(H,52,64)(H,53,59)(H,54,60)(H,55,65)(H,56,66);(H,6,7)/t27-,28-,35+,36+,37+,38+;/m1./s1

InChI key

KNKVMVJCRGCBFW-GJLSYRFBSA-N

Amino Acid Sequence

(Tyr-DAla-Gly-Phe-NH)2

Biochem/physiol Actions

Biphalin is a dimeric enkephalin that is a potent and non-selective opioid receptors (OR) agonist. It displays a high analgesic potency that is over 1000-fold greater than morphine. Studies show that biphalin exhibits neuroprotective effects in rat models of stroke.
Biphalin is a potent and non-selective opioid receptors (OR) agonist that displays neuroprotective effects in rat models of stroke.
Biphalin trifluoroacetate salt, a highly active synthetic octapeptide, is an analog of biphalin.[1] It displays a strong affinity in the nanomolar range for the receptors μ and δ.[2]

Features and Benefits

This compound is featured on the Opioid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
042M4747V

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Adriano Mollica et al.
Amino acids, 40(5), 1503-1511 (2010-10-07)
We report the synthesis and the biological evaluation of two new analogues of the potent dimeric opioid peptide biphalin. The performed modification is based on the replacement of two key structural elements of the native biphalin, namely: the hydrazine bridge
Adriano Mollica et al.
Journal of medicinal chemistry, 56(8), 3419-3423 (2013-04-04)
Natural residues of the dimeric opioid peptide Biphalin were replaced by the corresponding homo-β(3) amino acids. The derivative 1 containing hβ(3) Phe in place of Phe showed good μ- and δ-receptor affinities (Ki(δ) = 0.72 nM; Ki(μ) = 1.1 nM)

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