Erectile Function

1
HOT Functions of a-MSH Analogues

• Erectile Function
• Feeding Behavior--Obesity
• Pigmentation--Tanning
• Reproductive Ability
• Cardiovascular Function
• Learning
• Memory
• Immune Response

2
Brief History of a-MSH Analogues
3
Synthesis of WY012 by SPPS
4
UGLY Facts related to Boc-(1-Me)His

• COST US645/g
• Synthesis

Hydrophilicity assessed by HPLC (1-Me)His and
Boc-(1-Me)His (Column dead volume is around 3.2
minutes)
5
Proposed Tactics--Using DIEA Salts
6
Reality of the Synthesis of DIEA Salts
7
HPLC Analysis of Crude Peptides
a) From Boc-(1-Me)His-OH b) and c) From
Boc-(1-Me)-His DIEA and DIEA.HCl salts mix.

• Column Vydac C18 gradient 10-90 A in 40
  minutes A MeCN, B (0.1 TFA) H2O flow 1.0
  mL detection 230, 254, 280 nm.

8
Conclusions

• Mixture of Boc-(1-Me)His.DIEA and DIEA.HCl salts
  was Successfully Applied to Peptide Syntheses
• This Method has Various Advantages, Including
  Very Economic, Time-saving and Easy Access to
  Starting Materials
• This Method Should be Applicable to Other
  Hydrophilic Amino Acids

9
References and Acknowledgements

• 1. Eifler, S., Leblond, I., Trifilieff, E., and
  Lepoittevin, J.-P., Letters Pept. Sci., 4(1997)
  467.
• 2. Pennington, M.W., and Dunn, B.M., (Eds.),
  Peptide Synthesis Protocols, Humana Press Inc.,
  1994.
• 3. Miyazawa, T., Otomatsu, T. Yamada, T.
  Kuwata, S., Chem. Express, 4(1989) 745.
• Funded by Grants From US Public Health Service

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