Organic Chemistry

(Dana P.) #1
Section 23.10 Automated Peptide Synthesis 981

HF

CH 2

CH 3

CH 3 CCO 2

R R R

R R

H 2 NCHC NHCHC NHCHCO CH 2

OOO

+

+

+

HOCH 2

R

H 3 NCHC NHCHC NHCHCOH

OOO

+

CF 3 COOH
CH 2 Cl 2

CH 3

CH 3

CH 3 C

O

O C

R R

NHCHC NHCHCO CH 2

O

CH 2

CH 3

CH 3 CCO 2

RR

H 2 NCHC NHCHCO CH 2

OO

++

O

CF 3 COOH
CH 2 Cl 2

CH 3

CH 3

CH 3 C

O

O C NHCHCO CH 2

O

N-protected amino acid N-protected and
C-activated amino acid

DCC

CH 3

CH 3

CH 3 C

O

O C NHCHCOH

O

CH 3

CH 3

CH 3 C

O

O C

R R

R

R

NHCHCO DCC

O

CH 2

CH 3

CH 3 CCO 2 H 2 NCHCO CH 2

O

++

Tutorial:
Merrifield automated
solid-phase synthesis

N-protected amino acid N-protected and
C-activated amino acid

DCC

CH 3

CH 3

CH 3 C

O

O C

R

NHCHCOH

O

CH 3

CH 3

CH 3 C

O

O C

R

NHCHCO DCC

O

CF 3 COOH
CH 2 Cl 2

CH 3

CH 3

CH 3 C

O

O C

R R

NHCHC

R

NHCHC NHCHCO CH 2

O O O

BRUI23-959-998r2 29-03-2003 1:36 PM Page 981

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