МСОС Методичка

Раздел 3. Методы окисления органических соединений и методы формирования С-С и C=C-связей

3.1. Методы окисления органических

соединений																												14.
												CrO					/ H SO
	R						OH									3	2		4
1.
													Me CO, RT
																2
				OH								CrO					/ H SO
																3	2		4									15.
2.
													Me CO, RT
	R						R									2
	2						1
								CrO
3.	Ar-Me									3
								H SO
									2	4																		16.
																			CrO
4.	Ar-OH						or		Ar-NH											3
													2						H SO
																			2	4
																R
																	1		CrO									17.
																				3
5.																			H SO
																			2	4
															R
																2
	R ,			R	= H or Alk or Ar or OAlk
	1			2
										PCC or PDC or CrO											*2Py							18.
	R						OH
6.																				3
																	DCM, RT
			OH																KMnO
7.																				4								19.
					or		Ar				Me				H O or PhH (DCM)						/ 18-c-6 (TEBAC), T
	R
																2
			OH																KMnO
																					4
8.							or
							Ar							Ar			H O or PhH (DCM)					/ 18-c-6 (TEBAC), T
	R				R				1							2	2
	1					2																						20.
	R1
								R1							R2
																				KMnO4
9.							or
																		H2O
						R2
																		or PhH (DCM) / 18-c-6 (TEBAC), RT
	R							R1							R2													21.
	1
																				KMnO
10.							or															4
																		H O
						R
								R							R		2
							2		3									or PhH (DCM) / 18-c-6 (TEBAC),
																4
																		KMnO
				S															4									22.
11.	R1						R2		H O or PhH (DCM)											/ 18-c-6 (TEBAC)
										2
	R			, R		=Alk or Ar
	1			2
	R2					R3												OH										23.
12.									or													OH		MnO2
																		or
	R1							OH				Ar							ArHet					PhH,
									Rn										Rn
																								MnO	2			24.
13.	Rn						or												or			NH
																								PhH,
																					N
																		N
																					H
																		H

		O			Ag2O / NH4OH
R
		H
	O						R			R
							2			3
		OH					OH
					>		>
	R				Ar		R
							1
					OH
>						>		OH
		Alk	1		Alk	2	Alk
		OH			RuO2 or RuCl3 (cat.)

NaIO4 or NaClO R or K2S2O8 (eq.)

CCl4 / MecN / H2O

>

OH

Ag CO	3	/ целит
2

			OH			RuO		or RuCl						3	(cat.)
							2
R						NaIO			or NaClO
							4
						or K S O						(ex.)
							2		2		8
						CCl	/ MecN / H O
					4										2
			OH			RuO	or RuCl								(cat.)
							2						3
						NaIO			or NaClO
							4
						or K S O				8
R				R			2		2
1				2		CCl	/ MecN / H O
					4										2
HO				R		HO					R4				RuO		or RuCl (cat.)
				2												2
					or								R							3
													3		NaIO			or NaClO
						R
																	4
					2										or K S O					(ex.)
																			8
R				OH		R1					OH					2		2
1															CCl		/ MecN / H O
															4					2
		R				R	RuO				or RuCl (cat.)
			2						2						3
					3
								NaIO					or NaClO
											4
									or K S O (eq.)
		R									2		2		8
						R			CCl		/ MecN / H O
			1		4
R	-R		= H or Alk or Ar								4						2
1		4
			R
				2											OsO
															4
				or
R						R			R
					1						2
1
R				R		OsO (cat.) / NMO or K FeCN														or H O
3				4																	2
					4										3			6		2
									H O / t-BuOH
									2
R				R		Py or NEt							or MsNH			(cat.)
1				2
											3				2
R	-R		= H or Alk or Ar
1	4
RS				RM	AD-mix- or
						OsO4 / (DHQD)2PHAL (cat.) / NMO or K3FeCN6
RL											H2O / t-BuOH
RS				RM		AD-mix- or
						OsO4	/(DHQ)2PHAL (cat.) / NMO or K3FeCN6

RL H2O / t-BuOH

41

OH	OH	DMSO /

					or													2		2				38.
25.													DCC or (COCl) or SOCl									or TFAA
	R
														O
					R						R		NEt
														, -78 C -> RT
					1						2		3
	R2				R3		1. O3
																								39.
26.
	R1				R4		2. NaHSO3 or PPh3 or Zn / AcOH
	R1-R4 = H or Alk or Ar
	R				R
		2			3			1. O3																40.
27.	R				R			2. NaBH4
		1			4
	R	, R			= H or Alk or Ar
		1	4																					41.
					OH					OH				O / Pt(cat.)
														2
28.	R				>
						R							R
						1							2
					OH																			42.
29.	R					>		R									OH
																			O	/ Pt(cat.)
	n
										n								2
					OH			OH					TAPI (Dess-Martin periodinane)											43.
30.
	R				or
														DCM, RT
					R1						R2
								SeO					/ диоксан,
											2
	R				R																			44.
31.		1			2
	R =Ar or HerAr or alkenyl or acyl
		1
	R		= Alk > H
		2
	R				R																			45.
		2			3					H O / NaWO						(cat.)
											2		2	4
32.	R							PTC (Aliqat 336)
					R																			46.
	1				4
	R		-R		= H or Alk or Ar
		1	4
					OH						OH			H O				/ RuCl (cat.)
33.														2		2				3
	R				or																			47.
							R						R
								1					2
					OH						OH			H O			/	NaWO (cat.)
															2
														2						4
34.	R				or
							R						R	PTC (Aliqat 336)
								1					2
						H O					/ NaOH, RT
35.						2		2																48.
	R				N
				O
36.										Oxone
														O
						H O				/ NaHCO
														, 5 C
	Me				Me	2								3										49.
	R2				R3								Oxone
37.
	R1				R4					H2O / NaHCO3, 5OC														50.

R1-R4 = H or Alk or Ar

oxone

R

NH

2

NaHCO

3

O

Oxone

R1

R2

Al / DCM

R1, R2 = 3O > 2O > Bn > Ph >1O > Me

OH

OH

TBHP/ CrO (cat.)

or

3

R

R

R

1

2

R

R

2

3

TBHP

PTC (Triton B)

R

1

R

4

R

R

2

3

DDO

Me CO

R

R

2

1

4

DDO

R

H

Me CO

2

O

O

R = 3

(axial > equat.) >> 2

HO

R

2

DDO

O

R

OH

DCM, O C

1

DDO

R

NH2

Me2CO, RT

S

DDO

R

R

Me CO, RT

2

1

2

R

R

O

2

3

R

(MCPBA)

O

OH

R

R

1

4

R

-R

4

= H or Alk or Ar

1

O

MCPBA

R

R

1

2

R

, R

O

O

> Bn > Ph >1

O

> Me

2

= 3

> 2

1

HO

R2

HO

R4

NaIO4

or

R3

R2

MeOH / H2O

R1

OH

R1

OH

R2

R2

R3

NaIO4 / OsO4 (cat.)

or

R1

R

R

t-BuOH / H2O

1

4

42

51.

52.

53.

R2

R1

R2

R1 RL

R		R	R
3					TBHP
		2	3
	or				VO(AcAc)	2	(cat.)
OH
		R		OH	or Mo(CO) (cat.)
		1				6
R			R
4
			4
R = H or Alk or Ar
4
R				TBHP
3
		(+)-DET /		Ti(OPr) (cat.) /			MS
					4
OH		or	(-)-DET / Ti(OPr) (cat.) / MS
					4
R			NaClO
S
	(S,S) or (R,R)-Jacobsen's cat.
		3+	-salene complex)
	(Mn

3.2. Методы образования С-С-связей с помощью металлоорганических реагентов.

		Mg
54.	R	Hal
		Et O or THF
		2
	R= Alk or All or Bn or Ar ; Hal = I > Br >Cl
			R	-MgX
55.	1	H	2
	R		Et O or THF
			2
		2Li
56.	R	Hal
		hexane
	R= Alk or Ar ; Hal = I,			Br, Cl
	R	Alk-Li
		Hal		O
57.		Et O or THF, -78 C
		2
	R= Ar or HetAr or alkenyl ; Hal = I > Br

X

Ar or

BuLi or t-BuLi or LDA

HetAr

Et2O or THF, -78OC

H

Me

62.

N

Me

NMe2

X=

O

>

CF3 >

F

>

>

>

O

O >

OR

>

NMe

>

NMe2 > Br

2

R

O

63.

R2

2LDA

OH

R1

Et2O, -78OC

O

R

LTMP

64.

2

OR

O

3

Et O, -78 C

2

R

1

CO2

...

H

65. R

M

M = Li or MgX

O

R

66.

2

X

O

R

M

1

M = Li or MgHal; X= Cl or OR

2

58.

59.

60.

Bu-Li

B(OR )

H O/H

2

R

Hal

1

M

2 3

...

O

67.

R

Et O or THF or Trapp mix, -78 C

2

M = Li or MgHal

R= Ar or HetAr ; Hal = I > Br

R = Me or Et or i-Pr

2

2 t-BuLi

Me

R

Hal

O

Me

O

O

MeO

B

Et O or THF or Trapp mix, -78 C

or

2

MeO

B

O

68.

Me

R= 1

Alk or All or Bn or Ar or HetAr or Vin;

O

O

Hal = I > Br

R

M

Me

1

R

M = Li or MgHal

3

R

H

Ar

H

>

R

H >

2

>

R2

C

N

H O/H

69. R1

...

2

R

Bu-Li/TMEDA

M

R

S

1

or t-BuLi

Ar

M = Li or MgHal

2

>

NH >

H

Et O or THF, -78OC

>

H

2

O

S

R

1

Me

Me

Me

Me Bu-Li

70.

X

R

2

...

H2O/H

61.

or

R1

M

Me Et2O, -78OC

Me

N

Me Me

N

M = Li or MgHal

H

H

X= Cl or OR3 or NMe2 or N(Me)OMe

43

HC(OMe)

H O/H

71.

3

...

2

R

MgHal

R2

C

N

...

NaBH4

72.

R1

M

O

Et2O or THF, -78 C

M = Li or MgHal

O*BF

or

3

H O/H

O

73.

R

M

O ...

2

1

Et

O or THF, -78 C

2

M = Li or MgHal

O

74.

1

R2

R3

...

H2O/H

R

M

M = Li or MgHal; R

, R

= H or Alk or Ar or HetAr

2

3

O

1/2

75.

R2O

R3

H O/H

1

...

2

R

M

M = Li or MgHal; R

= Me or Et or Ar

2

O

76.

R2

R3

HBr/AcOH

MgBr

Et O or THF ...

2

R4

N

77.

R2

R3

H O/H

...

2

R1

M

M = Li or MgHal

O

Me

1.

R1

78.

H

1. R2

Li/Et2O

Me

OH

MgSO4/DCM

... 2. H2O/H

NH2

2. TMS-Cl/Py

Me

Me

R1

79.

NaIO4

R

N

H2O

2

H

OH

R

X

2

R

M

1

R = Alkynyl or Bn or All or 1,3-dithianyl-2

80.

1

M = Li or MgHal

R

= 1

O

O

Alk or 2 Alk or Bn or All

2

X= I or Br or OTs

R

O

2

R

M

H O/H

1

...

2

81.

R

H

3

M = Li or MgHal

R

4

R2

O

82.

R3

R5

R1

Li

...

H2O/H

R4

R5 = Alk or Ar or HetAr

R

O

2

R

MgHal

H O/H

1

...

2

83.

R

R

CeCl

(anh.)

3

5

3

R

R

= Alk or Ar or HetAr

4

5

R

O

2

R

MgHal

H O/H

1

...

2

84.

R

R

O

3

5

C

CuI/THF, -78

R

R

= Alk or Ar or HetAr

4

5

Ar

I

Cu

85.

or

ArHet

I

O

DMF, 150 C

CuI

86.

2 R

Li

THF

R

Li

CuCN

87.

THF

88.

CuCN

R

Li

Li

...

S

THF

MeO

1. BuLi

R Li

89.

Me

H

...

2. CuI

Me

CuI

90.

2 R

MgHal

THF

R2

X

R

Cu

R

Li

1

1

91.

MeO

or

X=OTf > OTs, I >> Br or OTs

Me

Сu

R1 Li

Me R1, R2 = Alk or Ar or HetAr or Alkenyl

44

92.

93.

94.

95.

96.

97.

98.

99.

	O
	Tf	O
	2
	R
	2
R	Py or 2,6-di(t-Bu)-4-Me-pyridine
1

R	M	R	2	X
1		CuI or Li CuCl				/ THF
					4
				2
M = Li or MgHal
R	O	O
	= 1 Alk or 2	Alk or Bn or All
2
X= I or Br

	Rs	O
	R		R		M
	M
	100.
	R	H	M = Li or MgHal
	L
	Rs	H
	RL		R3		M
	101.		M = Li or MgHal
	X	O

X= OR1 or NR1R2

								R
								2		3.3. Методы образования С-С-связей с
			R	Cu	R	Li
			1		1				O	помощью реакций кросс-сочетания,
								R
		MeO		or				3		катализируемых комплексами палладия
					Сu	R		Li						R			MgHal
															2
Me							1			R		X
			R	= Alk or Ar or HetAr or Alkenyl						1				Pd(PPh )			or PdCl (dppf)(cat.)
		Me								102.						4
															3			2
			1
				R
				2						R1= Ar or HetAr or Alkenyl; X= OTf,										I >	Br >> Cl
						O							R	B(OH) / Na CO				or Cs CO			or K PO	4
					R					R		X	2		2		2	3	2	3	3
										1
R		M			3									3 4			2				2
	1									103.			Pd(PPh )		or PdCl (dppf)(cat.), PrOH / H O,
				CuI or Li CuCl				/ THF
							4
					2					R ,R		= Ar or HetAr or Alkenyl; X= OTf,							I	> Br >> Cl
M = Li or MgHal
										1	2

								n
	R	Cu		R	Li					O
MeO		or					O
				Сu	R	Li	n=1-4
Me
Me	R = Alk or Ar or HetAr or Alkenyl
							O
	R	Cu		R	Li
	1			1			X		R
MeO		or								2
				Сu	R	Li
Me					1
Me	R , R			= Alk or Ar or HetAr or Alkenyl
		1	2
	X= Cl > H >> Alk or Ar or OR
							3
					R2 O
R1	Cu	R1	Li		R3		R5
MeO	or					R4		H2O/H
					R = Alk or Ar or HetAr ...
		Сu	R1 Li		5
Me
Me
					R2	O
				R3			R5
R	Cu	R	Li			R4			R6	X
MeO	or	1		R5 = Alk or Ar or HetAr ...					R6= Alk or Bn;
1
									X= OTs or I
		Сu		R1 Li					or	Br or Cl
Me
Me

R

B(OH)

2

/ Cs CO

or K PO

2

2

3

3

4

R

Cl

1

Pd (dba)

/ P(t-Bu)

or P(c-Hex) (cat.),

104.

2

3

3

3

dioxane / H O,

2

R ,R

2

= Ar or HetAr or Alkenyl;

1

105.

Catecholborane or DBBS

H O/H

R

...

2

HO

OH

or

106.

OH

Me

Me

HO

OH

Me

Me

R

B

Ph-H,

(-H O, azeotropic remooval)

2

OH

Me

Me

Me

O

O

Me

107.

Me

B

B

Me

O

O

R

X

Me

Me

AcOK / Pd(PPh3)4(cat.), DMSO, 90OC

R= Ar or HetAr or Alkenyl; X= OTf,

I >

Br

Me

O

Me

O

R2

B

or R2

B

108.

O

Me

O

R1

X

Me

K3PO4 / PdCl2(dppf)(cat.), PrOH/H2O,

R1,R2 = Ar or HetAr or Alkenyl; X= OTf,

I >

Br >> Cl

45

										R			/ B / Pd(0)cat. / T
											2
	R		X
	1
	R = Ar or HetAr or Alkenyl; X= OTf, I >																			Br >> Cl;
109.	1
	R = Acyl > CO R								> CO H > Ar or HetAr > H > OR													;
	2						2	3						2							3
	B = Na CO					3	or NEt				3		or Cs CO					or Ag CO
			2											2		3			2	3
	Pd(0) = Pd(PPh							)		or Pd(OAc)								/ PPh
							3 4									2			3
									R				/	B / Pd(0)cat. / T
											2
	R		Cl
	1
110.	R = Ar or HetAr
	1
	R = Acyl > CO R							3	> CO H > Ar or HetAr > H > OR												;
	2						2						2							3
	B = Cs			CO or Ag CO
			2		3			2					3
	Pd(0) = Pd (dba)							3	/	P(t-Bu)						or P(c-Hex)
					2									3					3
111.	R1		X						H										R2
					NEt3 / CuI(cat.) / PdCl2(PPh3)2(cat.), THF,
	R1= Ar or HetAr or Alkenyl; X= OTf, I > Br >> Cl
						R							R	3				HetAr
							2
								N							or				N
112.								H											H
	R		X
	1						t-BuOK /							Pd(0)cat., Ph-Me,
	R = Ar or HetAr ;								X= OTf,							I >		Br >> Cl;
	1
	Pd(0)= PdCl (dppf) or Pd (dba)																	3	/ BINAP
						2								2

3.4. Методы образования С=С связей

113.

Grubbs or Schrock cat.

R

2

R

R1

3

H, T

R

4

114.

HO

H

H = H SO

4

or H PO

4

or HBr or HCl

2

3

O

O

O

or (CO H)

2

or Burgess regent

3

2

> 2

> 1

R1

R2

H, T

R3

115.

R4

H = H2SO4 or H3PO4 or HBr or HCl

HO

R1-R4 = Alk or Ar

R2

R3

R1

R4

1. S=C=S / t-BuOK

T

116.

2. MeI

...

HO

H

3O > 2O > 1O

R2

R3

Ts-Cl or SOCl2

R1

R4

B, T

117.

Py / DCM

...

HO

H

3O > 2O > 1O B = t-BuOK or qinoline or DBU or KOH/EtOH

R	R
2	3		B, T
R1	R	4

118.

X

H

3

O

O

> 1

O

;

X = I > OTs, Br > Cl ;

> 2

B = KOH/EtOH or t-BuOK or qinoline or DBU or DABCO

R

R

R

R

O

1

2

1

2

DBU, 70-100 C

119.

or

Br

Ph-Me or DMF or DMSO

Br

Br

Br

B = KOH/EtOH or t-BuOK or qinoline or DBU or DABCO

R

2

PPh

B

X

3

...

120.

H

R1

R , R

= Alk or Ar or HetAr or Alkenyl

1

2

X = I > OTs, Br > Cl ;

B = BuLi or LDA or t-BuOK or NaH

PPh

3

O

121.

4S

3L

R

R

R

R

2S

1L

R

- R

= H or Alk or Ar or HetAr

1

4

H

O

O

122.

R

R

2S

1L

Ph P

X

3

X = OAlk or Alk or Ar;

R

,

R = H or Alk or Ar or HetAr

1

2

P(OMe)

3

or P(OEt)

3

R

X

123.

R

, R

2

= Alk or Ar or HetAr or Alkenyl

1

X = I

> OTs, Br > Cl ;

O

O

B

R

R

124.

R

P

2L

3S

OAlk

1

...

OAlk

DMF

R

= CO Alk or Ar or HetAr or Alkenyl

1

2

B = KOH or t-BuOK or NaH

O

O

O

125.

P

OCH2CF3

R2L

R3S

MeO

OCH2CF3

KHMDS / 18-c-6, THF

O

O

R3L

R4S

126. R1

1. LDA

P

OAlk

O ...

B, DMF

OAlk

2. R2

B = NaH or t-BuOK

R1-R4

= Alk or Ar or HetAr

OMe

46

Контрольная работа № 3,

Вариант1

I. Приведите структуру и укажите стереохимию продуктов реакций (3, 8*) (10 балов):

1.

2.

O
O	O
			RuCl		-NaIO
				3	4
		O	CCl	-MeCN-H		O
OH	O		4		2

	OH	O
EtO		NaIO
		4
		OEt
O	OH

3*.

	Me		OsO	-NMO
EtO		Et	4
			(DHQ) PHAL
			2
	O

4.

5.

6.

		O	Br	Br
EtO
			2 LTMP
		OEt
	O		Et2O -78oC
		O
			MgBr	HBr
MeO		OMe
		Li	Am	O
Me	O
			OTBDPS
Me		Cu		OTBDPS
Me			THF

7*.

O		O	Me-Li
Me	O
		H	Et O
Me
			2

MeO			Br	HN	NMe
8.				Pd(OAc)	, PPh	3
				2
				KO-t-Bu,Ph-Me 110 C
						0

9.

10

	OTf			CN
			Pd(OAc)2, PPh3
			NEt , DMF, 1000C
			3
				O O	OCH2-CF3
		O	MeO	P
					OCH2-CF3
O		H			o
			KHMDS, 18-c-6		0-5 C

II.Заполните схему превращений (10 балов):

O			O	O OMe
				P
			MeO			H2		полупродукт
OH	BH *THF	(COCl)		OMe			LiAlH
	3	2					4	для синтеза
		... DMSO ...					... Et O
BocN			NaH, DMF		...	Pd/C		... тирофибана
							2
		NEt3

47

1.

ЗАЧЕТНАЯ РАБОТА Вариант 1

I. Приведите структуру продуктов реакций и их стереохимию (в реакциях 6,7*) (10 балов):

O
1. HS	BF	-Et O	SH
H			Br	ТMS
	3	2
	2. BuLi
F

2.

3.

	OH	O	OMe
			OH
			OMe
HO		OH	TsOH, T
	OH

	O
		1. DPPA/NEt	, T
		3
N	OH	2. HCl/H O
Me		2

4.

5.

6*.

	Cbz	1. H-Phe-OBn, PyBop, DIEA
	Boc-Lys-OH
		2. TFA
	O	O	O
	2		H	H	NaOH	H+
	EtO	OEt
			Pip*AcOH, T		H O	T
					2
		O
			2-(Me)-CBS-
			-оксаборолидин
	F		BH	*THF
			3

7*.

O	t-BuOOH
OH	VO(AcAc)	2
O

8.

	Br
	LDA	O	+
			H
	Et O	BF
N	2	3
	O
	-78 C
			Me

9.

			TBDPSO			OTf
	O
		Me		Me	N	O
	O
			Me
	B				O	BnO
HO	O		Me		Pd (dba)	3
					2
		Me		Cs CO /DCM/DMF
				2	3

10	Br	1. PPh	O	NMe
		3
		2. BuLi

48

II. Заполните схему превращений (10 балов):

O

O

OMe

NH

Ac O

2

OsO -NMO

K CO

LiAlH

+

(1 экв)

CrO

CrO

3

H

4

2

4

...

...

...

3

...

...

3

...

...

O

Ph-H, T

...

(избыток)

Py

ацетон

MeOH

ацетон

(DHQD)2PHAL

(-H O)

кортизон

2

III. Заполните схему превращений (10 балов):

I

Me

Me

O

Br

Me

O

Me

Br

B

B

2 t-Bu-Li

1. B(OMe)

Me

O

O

Me

3

N

Me

Me

...

N

Et2O

2. H+

... Pd(OAc)

2 , PPh3

...

PdCl (dppf)

2

...

N

O

2

-78 C

Na CO

, T

KOAc

2

3

PdCl (dppf)

O

2

диоксан, 100 C

2

...

F

Na CO

3

2

O

O

GSK2126458

диоксан, 100 C

F

S

Cl

(ACS Med Chem Lett 2010)

H N

Br

2

O

...

NEt

MeO

N

3

49

Приложение. Строение и сокращенные обозначения белковых аминокислот.
		Заменимые						Незаменимые
№	Название		Структура			№	Название			Структура
1	Глицин		O			11	Валин			СH O
										3
	(Gly,G)	H N					(Val, V)
		2		OH					СH		OH
									3
										NH
										2
2	Аланин		O			12	Лейцин				O
	(Ala, A)	СН					(Leu, L)		СН
		3		OH					3		OH
			NH							СН	NH
			2							3	2
3	Пролин			O		13	Изолейцин			CH3 O
	(Pro, P)						(Ile, I)		H3C
		N		OH							OH
		H									NH2
4	Cерин			O		14	Треонин			OH	O
	(Ser, S)						(Thr, T)
		HO		OH					H C		OH
									3
			NH							NH
				2							2
5	Цистеин			O		15	Метионин				O
	(Cys, C)	HS		OH			(Met, M)		H C	S	OH
									3
			NH								NH
											2
				2
6	Тирозин					16	Фенилаланин
	(Tyr, Y)	HO			O		(Phe, F)				O
				H N	OH					H N	OH
				2						2
7	Аспарагиновая			O		17	Триптофан				O
	кислота	HO					(Trp, W)
	(Asp, D)			OH							OH
			O	NH2						N	NH
										H	2
8	Аспарагин			O		18	Гистидин		N
	(Asn, N)	H2N					(Hys, H)		N		O
				OH
									H	H2N	OH
			O	NH
				2
9	Глутаминовая		O	O		19	Лизин				O
	кислота						(Lys, K)	H N
	(Glu, E)	HO			OH			2			OH
				NH							NH
				2							2
10	Глутамин		O	O		20	Аргинин		NH2		O
	(Gln, Q)						(Arg, R)
		H2N			OH			HN	N		OH
				NH					H		NH2
				2
											50